Tricyclic benzoylpyrazole derivatives used as a herbicide

ABSTRACT

Tricyclic benzoylpyrazole derivatives of the formula I 
                         
wherein X, Y, R 1 , R 2 , R 6 , R 7 , R 3 , R 4 , R 5 , l, R 8  and R 9  are as defined in the disclosure and their agriculturally useful salts; processes and intermediates for preparing the tricyclic benzoylpyrazole derivatives; compositions comprising them and the use of these derivatives or of the compositions comprising them for controlling undesirable plants are described.

This application is a 371 of PCT/EP00/02010 filed Mar. 8, 2000.

The present invention relates to novel tricyclic benzoylpyrazolederivatives of the formula I

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;    -   Y together with the two carbons to which it is attached forms a        saturated, partially saturated or unsaturated 5- or 6-membered        heterocycle which contains one to three identical or different        heteroatoms selected from the following group:    -    oxygen, sulfur or nitrogen;    -   R¹,R²,R⁶,R⁷ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;    -   R³ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy or        C₁–C₆-haloalkoxy;    -   R⁴ is hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl,        C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy,        C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,        C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,        C₁–C₆-haloalkylsulfonyl, aminosulfonyl,        N-(C₁–C₆-alkyl)aminosulfonyl, N,N-di(C₁–C₆-alkyl)aminosulfonyl,        N-(C₁–C₆-alkylsulfonyl)amino, N-(C₁–C₆-haloalkylsulfonyl)amino,        N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino or        N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino;    -   R⁵ is hydrogen, C₁–C₆-alkyl or halogen;    -   R⁸ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkylcarbonyl, formyl, C₁–C₆-alkoxycarbonyl,        C₁–C₆-haloalkoxycarbonyl, C₁–C₆-alkylsulfonyl or        C₁–C₆-haloalkylsulfonyl;    -   l is 0, 1 or 2;    -   R⁹ is a radical IIa or IIb

-   -   where    -   R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴, NR¹⁵R¹⁶        or N-bonded heterocyclyl, where the heterocyclyl radical may be        partially or fully halogenated and/or may carry one to three of        the following radicals:    -    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   R¹¹ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₃–C₆-cycloalkyl,        hydroxyl, C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;    -   R¹² is hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        hydroxyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio or        C₁–C₆-haloalkylthio;    -   R¹³ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,        C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl,        C₁–C₂₀-alkylcarbonyl, C₂–C₂₀-alkenylcarbonyl,        C₂–C₆-alkynylcarbonyl, C₃–C₆-cycloalkylcarbonyl,        C₁–C₆-alkoxycarbonyl, C₃–C₆-alkenyloxycarbonyl,        C₃–C₆-alkynyloxycarbonyl, C₁–C₆-alkylthiocarbonyl,        C₁–C₆-alkylaminocarbonyl, C₃–C₆-alkenylaminocarbonyl,        C₃–C₆-alkynylaminocarbonyl, N,N-di(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,        N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,        di(C₁–C₆-alkyl)aminothiocarbonyl,        C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl, C₁–C₆-alkoxyimino-C₁–C₆-alkyl,        N-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl or        N,N-di(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, where the        abovementioned alkyl, cycloalkyl and alkoxy radicals may be        partially or fully halogenated and/or may carry one to three of        the following groups:    -    cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di(C₁–C₄-alkyl)amino,        C₁–C₄-alkylcarbonyl, C₁–C₄-akoxycarbonyl,        C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,        di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,        C₁–C₄-alkylaminocarbonyl, di(C₁–C₄-alkyl)aminocarbonyl,        aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;    -    is phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,        heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,        heterocyclylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl,        heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,        heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,        phenylaminocarbonyl, N-(C₁–C₆-alkyl)-N-(phenyl)aminocarbonyl,        heterocyclylaminocarbonyl,        N-(C₁–C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,        phenyl-C₂–C₆-alkenylcarbonyl or        heterocyclyl-C₂–C₆-alkenylcarbonyl, where the phenyl and the        heterocyclyl radical of the 18 lastmentioned substituents may be        partially or fully halogenated and/or may carry one to three of        the following radicals:    -    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy,        C₁–C₄-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where        the two lastmentioned substituents for their part may be        partially or fully halogenated and/or may carry one to three of        the following radicals:    -    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   R¹⁴ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,        C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl,        C₁–C₆-alkoxy, di(C₁–C₆-alkyl)amino or di(C₁–C₆-haloalkyl)amino,        where the abovementioned alkyl, cycloalkyl and alkoxy radicals        may be partially or fully halogenated and/or may carry one to        three of the following groups:    -    cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di(C₁–C₄-alkyl)amino,        C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,        C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,        di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,        C₁–C₄-alkylaminocarbonyl, di(C₁–C₄-alkyl)aminocarbonyl,        aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;    -    is phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,        heterocyclyl-C₁–C₆-alkyl, phenoxy, heterocyclyloxy, where the        phenyl and the heterocyclyl radical of the lastmentioned        substituents may be partially or fully halogenated and/or may        carry one to three of the following radicals:    -    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   R¹⁵ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,        C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl,        C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy,        di(C₁–C₆-alkyl)amino or C₁–C₆-alkylcarbonylamino, where the        abovementioned alkyl, cycloalkyl and alkoxy radicals may be        partially or fully halogenated and/or may carry one to three        radicals of the following group:    -    cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di(C₁–C₄-alkyl)amino,        C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,        C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,        di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,        C₁–C₄-alkylaminocarbonyl, di(C₁–C₄-alkyl)aminocarbonyl,        aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;    -    is phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl or        heterocyclyl-C₁–C₆-alkyl, where the phenyl or heterocyclyl        radical of the four lastmentioned substituents may be partially        or fully halogenated and/or may carry one to three of the        following radicals:    -    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   R¹⁶ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-alkynyl or        C₁–C₆-alkylcarbonyl;        and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates forpreparing compounds of the formula I, to compositions comprising them,and to the use of these derivatives or of the compositions comprisingthem for controlling harmful plants.

WO 97/19087 and EP-A 860 441 disclose tricyclic compounds which arecharacterized in that the respective benzoyl unit that they contain isfused via positions 3 and 4 with a bicycle. However, the herbicidalproperties of the prior-art compounds and their compatibility with cropplants are not entirely satisfactory. It is an object of the presentinvention to provide novel, biologically, in particular herbicidally,active compounds having improved properties.

We have found that this object is achieved by the tricyclicbenzoylpyrazole derivatives of the formula I and their herbicidalaction.

Furthermore, we have found processes and intermediates for synthesizingthe compounds of the formula I. Likewise, we have found herbicidalcompositions which comprise the compounds I and have very goodherbicidal action. Moreover, we have found processes for preparing thesecompositions and methods for controlling undesirable vegetation usingthe compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they are presentas enantiomers or diastereomer mixtures. The invention provides both thepure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of theiragriculturally useful salts, the type of salt generally beingimmaterial. Generally suitable are the salts of those cations or theacid addition salts of those acids whose cations and anions,respectively, do not negatively affect the herbicidal action of thecompounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, where,if desired, one to four hydrogen atoms may be replaced by C₁–C₄-alkyl,hydroxy-C₁–C₄-alkyl, C₁–C₄-alkoxy-C₁–C₄-alkyl,hydroxy-C₁–C₄-alkoxy-C₁–C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁–C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁–C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁–C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

In the case of R¹⁰=hydroxyl or mercapto, IIa also represents thetautomeric forms IIa′ and IIa″

Likewise, in the case of R¹⁰=hydroxyl or mercapto, IIb also representsthe tautomeric forms IIb′ and IIb″

The organic molecular moieties mentioned for the substituents R¹–R¹⁷ oras radicals on phenyl and heterocyclyl radicals are collective terms forindividual enumerations of the individual group members. All hydrocarbonchains, i.e. all alkyl, haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy,alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl,N,N-dialkylaminosulfonyl, N-alkylamino, N,N-dialkylamino,N-haloalkylamino, N,N-dihaloalkylamino, N-alkylsulfonylamino,N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino,N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy,alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl,alkoxyalkyl, hydroxyalkoxyalkyl, alkylcarbonylalkyl, alkoxyiminoalkyl,N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl,phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl,N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl,N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl,phenylcarbonylalkyl, heterocyclylcarbonylalkyl,dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl,alkenyloxycarbonyl, alkenylaminocarbonyl,N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl,alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl,N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl,alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy and alkynyloxymoieties, may be straight-chain or branched. Unless indicated otherwise,halogenated substituents preferably carry one to five identical ordifferent halogen atoms. The term halogen denotes in each case fluorine,chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁–C₄-alkyl and the alkyl moieties of hydroxy-C₁–C₄-alkyl: for        example methyl, ethyl, propyl, 1-methylethyl, butyl,        1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;    -   C₁–C₆-alkyl, and the alkyl moieties of        C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl, C₁–C₆-alkoxyimino-C₁–C₆-alkyl,        N-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl,        N-(di-C₁–C₆-alkylamino)imino-C₁–C₆-alkyl,        N-(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₁–C₆-alkyl)-N-phenylaminocarbonyl,        N-(C₁–C₆-alkyl)-N-heterocyclylaminocarbonyl, phenyl-C₁–C₆-alkyl,        N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino,        N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino,        heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,        heterocyclylcarbonyl-C₁–C₆-alkyl: C₁–C₄-alkyl as mentioned        above, and also, for example, pentyl, 1-methylbutyl,        2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,        hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,        2-methylpentyl, 3-methylpentyl, 4-methylpentyl,        1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,        2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,        1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,        1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;    -   C₁–C₄-haloalkyl: a C₁–C₄-alkyl radical as mentioned above which        is partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, i.e., for example, chloromethyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,        2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;    -   C₁–C₆-haloalkyl, and the haloalkyl moieties of        N-C₁–C₆-haloalkylamino and N,N-(di-C₁–C₆-haloalkyl)amino:        C₁–C₄-haloalkyl as mentioned above, and also, for example,        5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,        undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,        6-iodohexyl or dodecafluorohexyl;    -   C₁–C₄-alkoxy: for example methoxy, ethoxy, propoxy,        1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or        1,1-dimethylethoxy;    -   C₁–C₆-alkoxy, and the alkoxy moieties of        C₁–C₆-alkoxyimino-C₁–C₆-alkyl,        N-(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl and        N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)aminocarbonyl: C₁–C₄-alkoxy as        mentioned above, and also, for example, pentoxy, 1-methylbutoxy,        2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,        1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy,        hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,        4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,        1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,        3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,        1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,        1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;    -   C₁–C₄-haloalkoxy: a C₁–C₄-alkoxy radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example, fluoromethoxy,        difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,        bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,        2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,        2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,        2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,        2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,        3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,        2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,        2,3-difluoropropoxy, 2,3-dichloropropoxy,        3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,        2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,        1-(fluoromethyl)-2-fluoroethoxy,        1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,        4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or        nonafluorobutoxy;    -   C₁–C₆-haloalkoxy: C₁–C₄-haloalkoxy as mentioned above, and also,        for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,        5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy,        6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or        dodecafluorohexoxy;    -   C₁–C₄-alkylthio: for example methylthio, ethylthio, propylthio,        1-methylethylthio, butylthio, 1-methylpropylthio,        2-methylpropylthio or 1,1-dimethylethylthio;    -   C₁–C₆-alkylthio, and the alkylthio moieties of        C₁–C₆-alkylthiocarbonyl: C₁–C₄-alkylthio as mentioned above and        also, for example, pentylthio, 1-methylbutylthio,        2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio,        1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio,        1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio,        3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,        1,2-dimethylbutylthio, 1,3-dimethylbutylthio,        2,2-dimethylbutylthio, 2,3-dimethylbutylthio,        3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,        1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,        1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;    -   C₁–C₆-haloalkylthio: a C₁–C₆-alkylthio radical as mentioned        above which is partially or fully substituted by fluorine,        chlorine, bromine and/or iodine, i.e., for example,        fluoromethylthio, difluoromethylthio, trifluoromethylthio,        chlorodifluoromethylthio, bromodifluoromethylthio,        2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,        2-iodoethylthio, 2,2-difluoroethylthio,        2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,        2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,        2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,        2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,        3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,        2,2-difluoropropylthio, 2,3-difluoropropylthio,        2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,        3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,        heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,        1-(chloromethyl)-2-chloroethylthio,        1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,        4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio,        5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,        5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,        6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or        dodecafluorohexylthio;    -   C₁–C₆-alkylsulfinyl (C₁–C₆-alkyl-S(═O)—): for example        methylsulfinyl, ethylsulfinyl, propylsulfinyl,        1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl,        2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,        pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,        3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,        1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,        1,2-dimethylpropylsulfinyl, hexylsulfinyl,        1-methylpentylsulfinyl, 2-methylpentylsulfinyl,        3-methylpentylsulfinyl, 4-methylpentylsulfinyl,        1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,        1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,        2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,        1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,        1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,        1-ethyl-1-methylpropylsulfinyl or        1-ethyl-2-methylpropylsulfinyl;    -   C₁–C₆-haloalkylsulfinyl: a C₁–C₆-alkylsulfinyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, i.e., for example,        fluoromethylsulfinyl, difluoromethylsulfinyl,        trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl,        bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl,        2-chloroethylsulfinyl, 2-bromoethylsulfinyl,        2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,        2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,        2-chloro-2-fluoroethylsulfinyl,        2-chloro-2,2-difluoroethylsulfinyl,        2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,        2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,        2-chloropropylsulfinyl, 3-chloropropylsulfinyl,        2-bromopropylsulfinyl, 3-bromopropylsulfinyl,        2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,        2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,        3,3,3-trichloropropylsulfinyl,        2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,        1-(fluoromethyl)-2-fluoroethylsulfinyl,        1-(chloromethyl)-2-chloroethylsulfinyl,        1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,        4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,        nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,        5-chloropentylsulfinyl, 5-bromopentylsulfinyl,        5-iodopentylsulfinyl, undecafluoropentylsulfinyl,        6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,        6-bromohexylsulfinyl, 6-iodohexylsulfinyl or        dodecafluorohexylsulfinyl;    -   C₁–C₆-alkylsulfonyl (C₁–C₆-alkyl-S(═O)₂—), and the alkylsulfonyl        radicals of N-(C₁–C₆-alkylsulfonyl)amino and        N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino: for example        methylsulfonyl, ethylsulfonyl, propylsulfonyl,        1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,        2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl,        pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,        3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,        1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,        1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,        2-methylpentylsulfonyl, 3-methylpentylsulfonyl,        4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,        1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,        2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,        3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,        2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,        1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or        1-ethyl-2-methylpropylsulfonyl;    -   C₁–C₆-haloalkylsulfonyl, and the haloalkylsulfonyl radicals of        N-(C₁–C₆-haloalkylsulfonyl)amino and        N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino: a        C₁–C₆-alkylsulfonyl radical as mentioned above which is        partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, i.e., for example, fluoromethylsulfonyl,        difluoromethylsulfonyl, trifluoromethylsulfonyl,        chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,        2-fluoroethylsulfonyl, 2-chloroethylsulfonyl,        2-bromoethylsulfonyl, 2-iodoethylsulfonyl,        2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,        2-chloro-2-fluoroethylsulfonyl,        2-chloro-2,2-difluoroethylsulfonyl,        2,2-dichloro-2-fluoroethylsulfonyl,        2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,        2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,        2-chloropropylsulfonyl, 3-chloropropylsulfonyl,        2-bromopropylsulfonyl, 3-bromopropylsulfonyl,        2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,        2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,        3,3,3-trichloropropylsulfonyl,        2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,        1-(fluoromethyl)-2-fluoroethylsulfonyl,        1-(chloromethyl)-2-chloroethylsulfonyl,        1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,        4-chlorobutylsulfonyl, 4-bromobutylsulfonyl,        nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl,        5-chloropentylsulfonyl, 5-bromopentylsulfonyl,        5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,        6-bromohexylsulfonyl, 6-iodohexylsulfonyl or        dodecafluorohexylsulfonyl;    -   C₁–C₆-alkylamino, and the alkylamino radicals of        N-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl: for example methylamino,        ethylamino, propylamino, 1-methylethylamino, butylamino,        1-methylpropylamino, 2-methylpropylamino,        1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,        2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,        1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,        1,2-dimethylpropylamino, 1-methylpentylamino,        2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,        1,1-dimethylbutylamino, 1,2-dimethylbutylamino,        1,3-dimethylbutylamino, 2,2-dimethylbutylamino,        2,3-dimethylbutylamino, 3,3-dimethylbutylamino,        1-ethylbutylamino, 2-ethylbutylamino,        1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,        1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;    -   (C₁–C₆-alkylamino)sulfonyl: for example methylaminosulfonyl,        ethylaminosulfonyl, propylaminosulfonyl,        1-methylethylaminosulfonyl, butylaminosulfonyl,        1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl,        1,1-dimethylethylaminosulfonyl, pentylaminosulfonyl,        1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl,        3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl,        1-ethylpropylaminosulfonyl, hexylaminosulfonyl,        1,1-dimethylpropylaminosulfonyl,        1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl,        2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl,        4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl,        1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl,        2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl,        3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl,        2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl,        1,2,2-trimethylpropylaminosulfonyl,        1-ethyl-1-methylpropylaminosulfonyl or        1-ethyl-2-methylpropylaminosulfonyl;    -   di(C₁–C₆-alkyl)aminosulfonyl: for example        N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl,        N,N-di(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl,        N,N-dibutylaminosulfonyl, N,N-di(1-methylpropyl)aminosulfonyl,        N,N-di(2-methylpropyl)aminosulfonyl,        N,N-di(1,1-dimethylethyl)aminosulfonyl,        N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl,        N-methyl-N-(1-methylethyl)aminosulfonyl,        N-butyl-N-methylaminosulfonyl,        N-methyl-N-(1-methylpropyl)aminosulfonyl,        N-methyl-N-(2-methylpropyl)aminosulfonyl,        N-(1,1-dimethylethyl)-N-methylaminosulfonyl,        N-ethyl-N-propylaminosulfonyl,        N-ethyl-N-(1-methylethyl)aminosulfonyl,        N-butyl-N-ethylaminosulfonyl,        N-ethyl-N-(1-methylpropyl)aminosulfonyl,        N-ethyl-N-(2-methylpropyl)aminosulfonyl,        N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl,        N-(1-methylethyl)-N-propylaminosulfonyl,        N-butyl-N-propylaminosulfonyl,        N-(1-methylpropyl)-N-propylaminosulfonyl,        N-(2-methylpropyl)-N-propylaminosulfonyl,        N-(1,1-dimethylethyl)-N-propylaminosulfonyl,        N-butyl-N-(1-methylethyl)aminosulfonyl,        N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl,        N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl,        N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl,        N-butyl-N-(1-methylpropyl)aminosulfonyl,        N-butyl-N-(2-methylpropyl)aminosulfonyl,        N-butyl-N-(1,1-dimethylethyl)aminosulfonyl,        N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl,        N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl,        N-methyl-N-pentylaminosulfonyl,        N-methyl-N-(1-methylbutyl)aminosulfonyl,        N-methyl-N-(2-methylbutyl)aminosulfonyl,        N-methyl-N-(3-methylbutyl)aminosulfonyl,        N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl,        N-methyl-N-(1-ethylpropyl)aminosulfonyl,        N-methyl-N-hexylaminosulfonyl,        N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl,        N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl,        N-methyl-N-(1-methylpentyl)aminosulfonyl,        N-methyl-N-(2-methylpentyl)aminosulfonyl,        N-methyl-N-(3-methylpentyl)aminosulfonyl,        N-methyl-N-(4-methylpentyl)aminosulfonyl,        N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl,        N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl,        N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl,        N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl,        N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl,        N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl,        N-methyl-N-(1-ethylbutyl)aminosulfonyl,        N-methyl-N-(2-ethylbutyl)aminosulfonyl,        N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,        N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,        N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,        N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,        N-ethyl-N-pentylaminosulfonyl,        N-ethyl-N-(1-methylbutyl)aminosulfonyl,        N-ethyl-N-(2-methylbutyl)aminosulfonyl,        N-ethyl-N-(3-methylbutyl)aminosulfonyl,        N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl,        N-ethyl-N-(1-ethylpropyl)aminosulfonyl,        N-ethyl-N-hexylaminosulfonyl,        N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl,        N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl,        N-ethyl-N-(1-methylpentyl)aminosulfonyl,        N-ethyl-N-(2-methylpentyl)aminosulfonyl,        N-ethyl-N-(3-methylpentyl)aminosulfonyl,        N-ethyl-N-(4-methylpentyl)aminosulfonyl,        N-ethyl-N-(1,1-dimethylbutyl)aminosulfonyl,        N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl,        N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl,        N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl,        N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl,        N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl,        N-ethyl-N-(1-ethylbutyl)aminosulfonyl,        N-ethyl-N-(2-ethylbutyl)aminosulfonyl,        N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,        N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,        N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,        N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,        N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl,        N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl,        N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or        N,N-dihexylaminosulfonyl;    -   di(C₁–C₄-alkyl)amino, and the dialkylamino radicals of        di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl and        N-(di-C₁–C₄-alkylamino)imino-C₁–C₆-alkyl: for example        N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,        N,N-di(1-methylethyl)amino, N,N-dibutylamino,        N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,        N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,        N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,        N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,        N-methyl-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,        N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,        N-ethyl-N-(1-methylpropyl)amino,        N-ethyl-N-(2-methylpropyl)amino,        N-ethyl-N-(1,1-dimethylethyl)amino,        N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,        N-(1-methylpropyl)-N-propylamino,        N-(2-methylpropyl)-N-propylamino,        N-(1,1-dimethylethyl)-N-propylamino,        N-butyl-N-(1-methylethyl)amino,        N-(1-methylethyl)-N-(1-methylpropyl)amino,        N-(1-methylethyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,        N-butyl-N-(1-methylpropyl)amino,        N-butyl-N-(2-methylpropyl)amino,        N-butyl-N-(1,1-dimethylethyl)amino,        N-(1-methylpropyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or        N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;    -   di(C₁–C₆-alkyl)amino, and the dialkylamino radicals of        di(C₁–C₆-alkyl)aminoimino-C₁–C₆-alkyl: di(C₁–C₄-alkyl)amino as        mentioned above, and also N,N-dipentylamino, N,N-dihexylamino,        N-methyl-N-pentylamino, N-ethyl-N-pentylamino,        N-methyl-N-hexylamino or N-ethyl-N-hexylamino;    -   C₁–C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl,        propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,        1-methylpropylcarbonyl, 2-methylpropylcarbonyl or        1,1-dimethylethylcarbonyl;    -   C₁–C₆-alkylcarbonyl, and the alkylcarbonyl radicals of        C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl: C₁–C₄-alkylcarbonyl as        mentioned above, and also, for example, pentylcarbonyl,        1-methylbutylcarbonyl, 2-methylbutylcarbonyl,        3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl,        1-ethylpropylcarbonyl, hexylcarbonyl,        1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,        1-methylpentylcarbonyl, 2-methylpentylcarbonyl,        3-methylpentylcarbonyl, 4-methylpentylcarbonyl,        1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl,        1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl,        2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl,        1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,        1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,        1-ethyl-1-methylpropylcarbonyl or        1-ethyl-2-methylpropylcarbonyl;    -   C₁–C₂₀-alkylcarbonyl: C₁–C₆-alkylcarbonyl as mentioned above,        and also heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or        heptadecylcarbonyl;    -   C₁–C₄-alkoxycarbonyl, and the alkoxycarbonyl moieties of        di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl: for example        methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,        1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl,        2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;    -   (C₁–C₆-alkoxy)carbonyl: (C₁–C₄-alkoxy)carbonyl as mentioned        above, and also, for example, pentoxycarbonyl,        1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,        3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl,        1-ethylpropoxycarbonyl, hexoxycarbonyl,        1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,        1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,        3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,        1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,        1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,        2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,        1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,        1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,        1-ethyl-1-methyl-propoxycarbonyl or        1-ethyl-2-methyl-propoxycarbonyl;    -   C₁–C₆-haloalkoxycarbonyl: a C₁–C₆-alkoxycarbonyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, i.e., for example,        fluoromethoxycarbonyl, difluoromethoxycarbonyl,        trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl,        bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl,        2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,        2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,        2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,        2-chloro-2,2-difluoroethoxycarbonyl,        2,2-dichloro-2-fluoroethoxycarbonyl,        2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl,        2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl,        2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl,        2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,        2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,        2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,        3,3,3-trichloropropoxycarbonyl,        2,2,3,3,3-pentafluoropropoxycarbonyl,        heptafluoropropoxycarbonyl,        1-(fluoromethyl)-2-fluoroethoxycarbonyl,        1-(chloromethyl)-2-chloroethoxycarbonyl,        1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,        4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl,        nonafluorobutoxycarbonyl, 5-fluoropentoxycarbonyl,        5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl,        5-iodopentoxycarbonyl, 6-fluorohexoxycarbonyl,        6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl or        dodecafluorohexoxycarbonyl;    -   (C₁–C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,        propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy,        1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or        1,1-dimethylethylcarbonyloxy;    -   (C₁–C₄-alkylamino)carbonyl: for example methylaminocarbonyl,        ethylaminocarbonyl, propylaminocarbonyl,        1-methylethylaminocarbonyl, butylaminocarbonyl,        1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or        1,1-dimethylethylaminocarbonyl;    -   (C₁–C₆-alkylamino)carbonyl: (C₁–C₄-alkylamino)carbonyl as        mentioned above, and also, for example, pentylaminocarbonyl,        1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,        3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,        1-ethylpropylaminocarbonyl, hexylaminocarbonyl,        1,1-dimethylpropylaminocarbonyl,        1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,        2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,        4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,        1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,        2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,        3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,        2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,        1,2,2-trimethylpropylaminocarbonyl,        1-ethyl-1-methylpropylaminocarbonyl or        1-ethyl-2-methylpropylaminocarbonyl;    -   di(C₁–C₄-alkyl)aminocarbonyl: for example        N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,        N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl,        N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl,        N,N-di(2-methylpropyl)aminocarbonyl,        N,N-di(1,1-dimethylethyl)aminocarbonyl,        N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,        N-methyl-N-(1-methylethyl)aminocarbonyl,        N-butyl-N-methylaminocarbonyl,        N-methyl-N-(1-methylpropyl)aminocarbonyl,        N-methyl-N-(2-methylpropyl)aminocarbonyl,        N-(1,1-dimethylethyl)-N-methylaminocarbonyl,        N-ethyl-N-propylaminocarbonyl,        N-ethyl-N-(1-methylethyl)aminocarbonyl,        N-butyl-N-ethylaminocarbonyl,        N-ethyl-N-(1-methylpropyl)aminocarbonyl,        N-ethyl-N-(2-methylpropyl)aminocarbonyl,        N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,        N-(1-methylethyl)-N-propylaminocarbonyl,        N-butyl-N-propylaminocarbonyl,        N-(1-methylpropyl)-N-propylaminocarbonyl,        N-(2-methylpropyl)-N-propylaminocarbonyl,        N-(1,1-dimethylethyl)-N-propylaminocarbonyl,        N-butyl-N-(1-methylethyl)aminocarbonyl,        N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,        N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,        N-butyl-N-(1-methylpropyl)aminocarbonyl,        N-butyl-N-(2-methylpropyl)aminocarbonyl,        N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,        N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or        N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;    -   di(C₁–C₆-alkyl)aminocarbonyl: di(C₁–C₄-alkyl)aminocarbonyl as        mentioned above, and also, for example,        N-methyl-N-pentylaminocarbonyl,        N-methyl-N-(1-methylbutyl)aminocarbonyl,        N-Methyl-N-(2-methylbutyl)aminocarbonyl,        N-methyl-N-(3-methylbutyl)aminocarbonyl,        N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,        N-methyl-N-(1-ethylpropyl)aminocarbonyl,        N-methyl-N-hexylaminocarbonyl,        N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl,        N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,        N-methyl-N-(1-methylpentyl)aminocarbonyl,        N-methyl-N-(2-methylpentyl)aminocarbonyl,        N-methyl-N-(3-methylpentyl)aminocarbonyl,        N-methyl-N-(4-methylpentyl)aminocarbonyl,        N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,        N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,        N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,        N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,        N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,        N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,        N-methyl-N-(1-ethylbutyl)aminocarbonyl,        N-methyl-N-(2-ethylbutyl)aminocarbonyl,        N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,        N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,        N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,        N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,        N-ethyl-N-pentylaminocarbonyl,        N-ethyl-N-(1-methylbutyl)aminocarbonyl,        N-ethyl-N-(2-methylbutyl)aminocarbonyl,        N-ethyl-N-(3-methylbutyl)aminocarbonyl,        N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,        N-ethyl-N-(1-ethylpropyl)aminocarbonyl,        N-ethyl-N-hexylaminocarbonyl,        N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,        N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,        N-ethyl-N-(1-methylpentyl)aminocarbonyl,        N-ethyl-N-(2-methylpentyl)aminocarbonyl,        N-ethyl-N-(3-methylpentyl)aminocarbonyl,        N-ethyl-N-(4-methylpentyl)aminocarbonyl,        N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(1-ethylbutyl)aminocarbonyl,        N-ethyl-N-(2-ethylbutyl)aminocarbonyl,        N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,        N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,        N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,        N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,        N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,        N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl,        N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or        N,N-dihexylaminocarbonyl;    -   di(C₁–C₆-alkyl)aminothiocarbonyl: for example        N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,        N,N-di(1-methylethyl)aminothiocarbonyl,        N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl,        N,N-di(1-methylpropyl)aminothiocarbonyl,        N,N-di(2-methylpropyl)aminothiocarbonyl,        N,N-di(1,1-dimethylethyl)aminothiocarbonyl,        N-ethyl-N-methylaminothiocarbonyl,        N-methyl-N-propylaminothiocarbonyl,        N-methyl-N-(1-methylethyl)aminothiocarbonyl,        N-butyl-N-methylaminothiocarbonyl,        N-methyl-N-(1-methylpropyl)aminothiocarbonyl,        N-methyl-N-(2-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,        N-ethyl-N-propylaminothiocarbonyl,        N-ethyl-N-(1-methylethyl)aminothiocarbonyl,        N-butyl-N-ethylaminothiocarbonyl, N-ethyl        N-(1-methylpropyl)aminothiocarbonyl,        N-ethyl-N-(2-methylpropyl)aminothiocarbonyl,        N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl,        N-(1-methylethyl)-N-propylaminothiocarbonyl,        N-butyl-N-propylaminothiocarbonyl,        N-(1-methylpropyl)-N-propylaminothiocarbonyl,        N-(2-methylpropyl)-N-propylaminothiocarbonyl,        N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,        N-butyl-N-(1-methylethyl)aminothiocarbonyl,        N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,        N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,        N-butyl-N-(1-methylpropyl)aminothiocarbonyl,        N-butyl-N-(2-methylpropyl)aminothiocarbonyl,        N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,        N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,        N-methyl-N-pentylaminothiocarbonyl,        N-methyl-N-(1-methylbutyl)aminothiocarbonyl,        N-methyl-N-(2-methylbutyl)aminothiocarbonyl,        N-methyl-N-(3-methylbutyl)aminothiocarbonyl,        N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,        N-methyl-N-hexylaminothiocarbonyl,        N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1-methylpentyl)aminothiocarbonyl,        N-methyl-N-(2-methylpentyl)aminothiocarbonyl,        N-methyl-N-(3-methylpentyl)aminothiocarbonyl,        N-methyl-N-(4-methylpentyl)aminothiocarbonyl,        N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,        N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,        N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,        N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,        N-ethyl-N-pentylaminothiocarbonyl,        N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,        N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,        N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,        N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,        N-ethyl-N-hexylaminothiocarbonyl,        N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,        N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,        N-propyl-N-pentylaminothiocarbonyl,        N-butyl-N-pentylaminothiocarbonyl,        N,N-dipentylaminothiocarbonyl,        N-propyl-N-hexylaminothiocarbonyl,        N-butyl-N-hexylaminothiocarbonyl,        N-pentyl-N-hexylaminothiocarbonyl or        N,N-dihexylaminothiocarbonyl;    -   C₁–C₄-alkoxy-C₁–C₄-alkyl and the alkoxyalkyl moieties of        hydroxy-C₁–C₄-alkoxy-C₁–C₄-alkyl: C₁–C₄-alkyl which is        substituted by C₁–C₄-alkoxy as mentioned above, i.e., for        example, methoxymethyl, ethoxymethyl, propoxymethyl,        (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,        (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,        2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,        2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,        2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,        2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,        2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,        2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,        2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,        3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,        3-(1-methylethoxy)propyl, 3-(butoxy)propyl,        3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,        3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,        2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,        2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,        2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,        3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,        3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,        3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,        4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,        4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or        4-(1,1-dimethylethoxy)butyl;    -   C₁–C₄-alkoxy-C₁–C₄-alkoxy as alkoxyalkoxy moieties of        C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl: C₁–C₄-alkoxy which is        substituted by C₁–C₄-alkoxy as mentioned above, i.e., for        example, methoxymethoxy, ethoxymethoxy, propoxymethoxy,        (1-methylethoxy)methoxy, butoxymethoxy,        (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy,        (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy,        2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy,        2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy,        2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy,        2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy,        2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,        2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,        2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy,        3-(ethoxy)propoxy, 3-(propoxy)propoxy,        3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,        3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,        3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy,        2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy,        2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy,        2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy,        3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy,        3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,        3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,        3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy,        4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy,        4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy,        4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;    -   C₃–C₆-alkenyl, and the alkenyl moieties of        C₃–C₆-alkenylcarbonyl, C₃–C₆-alkenyloxy,        C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkenylaminocarbonyl,        N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl: for example        prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl,        2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl,        1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl,        2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,        1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,        3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,        1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl,        hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,        1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,        3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,        1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,        3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,        1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,        1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,        1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,        2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,        2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,        1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,        2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,        1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or        1-ethyl-2-methylprop-2-en-1-yl;    -   C₂–C₆-alkenyl, and the alkenyl moieties of        C₂–C₆-alkenylcarbonyl, phenyl-C₂–C₆-alkenylcarbonyl and        heterocyclyl-C₂–C₆-alkenylcarbonyl: C₃–C₆-alkenyl as mentioned        above, and also ethenyl;    -   C₂–C₂₀-alkenyl as alkenyl moiety of C₂–C₂₀-alkenylcarbonyl:        C₂–C₆-alkenyl as mentioned above, and also pentadecenyl or        heptadecenyl;    -   C₃–C₆-haloalkenyl: a C₃–C₆-alkenyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example, 2-chloroallyl,        3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,        2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl,        3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,        2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;    -   C₃–C₆-alkynyl, and the alkynyl moieties of        C₃–C₆-alkynylcarbonyl, C₃–C₆-alkynyloxy,        C₃–C₆-alkynyloxycarbonyl, C₃–C₆-alkynylaminocarbonyl,        N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,        N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxyamino)carbonyl: for example        propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl,        pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,        pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,        3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl,        hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl,        hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,        3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,        3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or        4-methylpent-2-yn-5-yl;    -   C₂–C₆-alkynyl, and the alkynyl moieties of        C₂–C₆-alkynylcarbonyl: C₃–C₆-alkynyl as mentioned above, and        also ethynyl;    -   C₃–C₆-haloalkynyl: a C₃–C₆-alkynyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example,        1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl,        4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,        1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl,        5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl,        6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;    -   C₃–C₆-cycloalkyl, and the cycloalkyl moieties of        C₃–C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl,        cyclopentyl or cyclohexyl;    -   heterocyclyl, and the heterocyclyl moieties of heterocyclyloxy,        heterocyclylcarbonyl, heterocyclyl-C₁–C₆-alkyl,        heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,        heterocyclyl-C₂–C₆-alkenylcarbonyl,        heterocyclylcarbonyl-C₁–C₆-alkyl,        N-(C₁–C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,        heterocyclylaminocarbonyl: a saturated, partially saturated or        unsaturated 5- or 6-membered heterocyclic ring which is attached        via carbon and contains one to four identical or different        heteroatoms selected from the following group: oxygen, sulfur        and nitrogen, i.e., for example, 5-membered rings having, for        example, one heteroatom, having two heteroatoms, having three        heteroatoms or having four heteroatoms or, for example,        6-membered rings having, for example, one heteroatom, having two        heteroatoms, having three heteroatoms or having four        heteroatoms, i.e. 5-membered rings having one heteroatom, such        as:    -   tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydrothien-2-yl, tetrahydrothien-3-yl,        tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl,        2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl,        2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl,        4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl,        2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,        2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl,        4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl,        2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl,        2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl,        4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl,        3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl,        3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl,        3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;    -   5-membered rings having two heteroatoms such as:    -   tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl,        tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl,        tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl,        1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl,        tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl,        tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl,        1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl,        tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl,        tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl,        tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl,        tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl,        1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl,        1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl,        4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl,        4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl,        2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl,        4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,        4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl,        2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl,        2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl,        2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl,        4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl,        2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl,        2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl,        2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl,        Δ³-1,2-dithiol-3-yl, Δ³-1,2-dithiol-4-yl, Δ³-1,2-dithiol-5-yl,        4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl,        4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl,        2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl,        2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl,        4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl,        4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl,        2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl,        2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl,        2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl,        4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,        2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,        2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl,        2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,        1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl,        1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl,        1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl,        isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl,        isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl,        oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl or        thiazol-5-yl;    -   5-membered rings having three heteroatoms such as:    -   1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl,        1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl,        1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl,        1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl,        1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl,        1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl,        1,2,3-Δ²-thiadiazolin-4-yl, 1,2,3-Δ²-thiadiazolin-5-yl,        1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl,        1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl,        1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl,        1,3,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl,        1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,        1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl,        1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl,        1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl,        1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-2-yl,        1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl,        2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl,        1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,        1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl,        1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl,        1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl,        1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl,        1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;    -   5-membered rings having four heteroatoms such as:    -   tetrazol-5-yl;    -   6-membered rings having one heteroatom such as:    -   tetrahydropyran-2-yl, tetrahydropyran-3-yl,        tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl,        piperidin-4-yl, tetrahydrothiopyran-2-yl,        tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl,        2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl,        2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl,        2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl,        2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl,        2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl,        1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl,        1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl,        1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl,        2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl,        2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl,        2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl,        2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl,        2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl,        1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl,        1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl,        2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl,        2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl,        2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl,        4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl,        4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl,        1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl,        2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl,        2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl,        2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl,        1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl,        1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl,        3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl,        3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl,        3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl,        2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl,        2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl,        2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl,        2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl,        2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or        pyridin-4-yl;    -   6-membered rings having two heteroatoms such as:    -   1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl,        1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl,        1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl,        1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl,        1,4-oxathian-2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl,        1,2-dithian-4-yl, hexahydropyrimidin-2-yl,        hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl,        hexahydropyrazin-2-yl, hexahydropyridazin-3-yl,        hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl,        tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl,        tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl,        tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl,        tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl,        tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl,        tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl,        tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl,        tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl,        2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl,        2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl,        2H-5,6-dihydro-1,2-thiazin-4-yl,        2H-5,6-dihydro-1,2-thiazin-5-yl,        2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl,        4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl,        4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl,        4H-5,6-dihydro-1,2-thiazin-4-yl,        4H-5,6-dihydro-1,2-thiazin-5-yl,        4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl,        2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl,        2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl,        2H-3,6-dihydro-1,2-thiazin-4-yl,        2H-3,6-dihydro-1,2-thiazin-5-yl,        2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl,        2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl,        2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl,        2H-3,4-dihydro-1,2-thiazin-4-yl,        2H-3,4-dihydro-1,2-thiazin-5-yl,        2H-3,4-dihydro-1,2-thiazin-6-yl,        2,3,4,5-tetrahydropyridazin-3-yl,        2,3,4,5-tetrahydropyridazin-4-yl,        2,3,4,5-tetrahydropyridazin-5-yl,        2,3,4,5-tetrahydropyridazin-6-yl,        3,4,5,6-tetrahydropyridazin-3-yl,        3,4,5,6-tetrahydropyridazin-4-yl,        1,2,5,6-tetrahydropyridazin-3-yl,        1,2,5,6-tetrahydropyridazin-4-yl,        1,2,5,6-tetrahydropyridazin-5-yl,        1,2,5,6-tetrahydropyridazin-6-yl,        1,2,3,6-tetrahydropyridazin-3-yl,        1,2,3,6-tetrahydropyridazin-4-yl,        4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl,        4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl,        4H-5,6-dihydro-1,3-thiazin-2-yl,        4H-5,6-dihydro-1,3-thiazin-4-yl,        4H-5,6-dihydro-1,3-thiazin-5-yl,        4H-5,6-dihydro-1,3-thiazin-6-yl,        3,4,5,6-tetrahydropyrimidin-2-yl,        3,4,5,6-tetrahydropyrimidin-4-yl,        3,4,5,6-tetrahydropyrimidin-5-yl,        3,4,5,6-tetrahydropyrimidin-6-yl,        1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl,        1,2,3,4-tetrahydropyrimidin-2-yl,        1,2,3,4-tetrahydropyrimidin-4-yl,        1,2,3,4-tetrahydropyrimidin-5-yl,        1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl,        2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl,        2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl,        2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl,        2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl,        2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl,        4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl,        4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl,        6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl,        6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl,        6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl,        2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl,        2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl,        2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl,        4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl,        4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl,        6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl,        6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl,        6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl,        2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl,        2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl,        2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl,        4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl,        1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl,        1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl,        1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl,        1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl,        1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl,        1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl,        1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl,        3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or        3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl,        pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;    -   6-membered rings having three heteroatoms such as:    -   1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,        1,2,4-triazin-6-yl;    -   6-membered rings having four heteroatoms such as:    -   1,2,4,5-tetrazin-3-yl;    -   where, if appropriate, the sulfur of the abovementioned        heterocycles may be oxidized to S═O or S(═O)₂    -   and where a bicyclic ring system may be formed with a fused-on        phenyl ring or with a C₃–C₆-carbocycle or with a further 5- to        6-membered heterocycle.    -   N-bonded heterocyclyl: a saturated, partially saturated or        unsaturated 5- or 6-membered heterocyclic ring which is attached        via nitrogen and contains at least one nitrogen and, if        appropriate, one to three identical or different heteroatoms        selected from the following group: oxygen, sulfur and nitrogen,        i.e., for example,    -   N-bonded 5-membered rings such as:    -   tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl,        2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl,        tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl,        tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl,        tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl,        2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl,        2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl,        2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl,        4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl,        2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl,        2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl,        1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl,        1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl,        1,2,4-Δ⁵-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl,        1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl,        1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-1-yl,        1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl,        1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl,        tetrazol-1-yl;    -   and also N-bonded 6-membered rings such as:    -   piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl,        1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl,        1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl,        hexahydropyrazin-1-yl, hexahydropyridazin-1-yl,        tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl,        tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl,        tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl,        2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl,        2H-3,6-dihydro-1,2-thiazin-2-yl, 2H-3,4-dihydro-1,2-oxazin-2-yl,        2H-3,4-dihydro-1,2-thiazin-2-yl,        2,3,4,5-tetrahydropyridazin-2-yl,        1,2,5,6-tetrahydropyridazin-1-yl,        1,2,5,6-tetrahydropyridazin-2-yl,        1,2,3,6-tetrahydropyridazin-1-yl,        3,4,5,6-tetrahydropyrimidin-3-yl,        1,2,3,4-tetrahydropyrazin-1-yl,        1,2,3,4-tetrahydropyrimidin-1-yl,        1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl,        2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl,        4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl,        1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl,        1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl;    -   and also N-bonded cyclic imides such as:    -   phthalimide, tetrahydrophthalimide, succinimide, maleimide,        glutarimide, 5-oxotriazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl        or 2,4-dioxo-(1H, 3H)-pyrimidin-3-yl;    -   where a bicyclic ring system may be formed with a fused-on        phenyl ring or with a C₃–C₆-carbocycle or a further 5- to        6-membered heterocycle.

All phenyl rings, heterocyclyl or N-heterocyclyl radicals and all phenylcomponents in phenoxy, phenyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl,phenyloxythiocarbonyl, phenylaminocarbonyl andN-(C₁–C₆-alkyl)-N-phenylaminocarbonyl or heterocyclyl components inheterocyclyloxy, heterocyclyl-C₁–C₆-alkyl,heterocyclylcarbonyl-C₁–C₆-alkyl, heterocyclylcarbonyl,heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl,heterocyclyloxycarbonyl, heterocyclylaminocarbonyl andN-(C₁–C₆-alkyl)-N-heterocyclylaminocarbonyl are, unless statedotherwise, preferably unsubstituted, or they carry one to three halogenatoms and/or one nitro group, one cyano radical and/or one or twomethyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.

Furthermore, the expression “Y together with the two carbons to which itis attached forms a saturated, partially saturated or unsaturatedheterocycle which contains one to three identical or differentheteroatoms selected from the following group: oxygen, sulfur andnitrogen” denotes, for example, 5-membered rings having one heteroatomsuch as:

tetrahydrofurandiyl, tetrahydrothienediyl, tetrahydropyrrolediyl,dihydrofurandiyl, dihydrothienediyl, dihydropyrrolediyl, furandiyl,thienediyl or pyrrolediyl;

or 5-membered rings having two heteroatoms such as:

tetrahydropyrazolediyl, tetrahydroisoxazolediyl, 1,2-oxathiolanediyl,tetrahydroisothiazolediyl, 1,2-dithiolanediyl, tetrahydroimidazolediyl,tetrahydrooxazolediyl, tetrahydrothiazolediyl, 1,3-dioxolanediyl,1,3-oxathiolanediyl, dihydropyrazolediyl, dihydroisoxazolediyl,dihydroisothiazolediyl, 1,2-dithiolediyl, dihydroimidazolediyl,dihydrooxazolediyl, dihydrothiazolediyl, dioxolediyl, oxathiolediyl,pyrazolediyl, isoxazolediyl, isothiazolediyl, imidazolediyl, oxazolediylor thiazolediyl;or 5-membered rings having three heteroatoms such as:1,2,3-oxadiazolinediyl, 1,2,3-thiadiazolinediyl, 1,2,3-triazolinediyl,1,2,3-oxadiazolediyl, 1,2,3-thiadiazolediyl or 1,2,3-triazolediyl;or 6-membered rings having one heteroatom such as:tetrahydropyrandiyl, piperidinediyl, tetrahydrothiopyrandiyl,dihydropyrandiyl, dihydrothiopyrandiyl, tetrahydropyridinediyl,pyrandiyl, thiopyrandiyl, dihydropyrinediyl or pyridinediyl;or 6-membered rings having two heteroatoms such as:1,3-dioxanediyl, 1,4-dioxanediyl, 1,3-dithianediyl, 1,4-dithianediyl,1,3-oxathianediyl, 1,4-oxathianediyl, 1,2-dithianediyl,hexahydropyrimidinediyl, hexahydropyrazinediyl, hexahydropyridazinediyl,tetrahydro-1,3-oxazinediyl, tetrahydro-1,3-thiazinediyl,tetrahydro-1,4-oxazinediyl, tetrahydro-1,2-oxazinediyl,dihydro-1,2-oxazinediyl, dihydro-1,2-thiazinediyl,tetrahydropyridazinediyl, dihydro-1,3-oxazinediyl,dihydro-1,3-oxazinediyl, dihydro-1,3-thiazinediyl,tetrahydropyrimidinediyl, tetrahydropyrazinediyl,dihydro-1,4-thiazinediyl, dihydro-1,4-oxazinediyl,dihydro-1,4-dioxinediyl, dihydro-1,4-dithiinediyl, 1,2-oxazinediyl,1,2-thiazinediyl, 1,3-oxazinediyl, 1,3-thiazinediyl, 1,4-oxazinediyl,1,4-thiazinediyl, dihydropyridazinediyl, dihydropyrazinediyl,dihydropyrimidinediyl, pyridazinediyl, pyrimidinediyl or pyrazinediyl;or 6-membered rings having 3 heteroatoms such as:1,2,4-triazinediyl;where, if appropriate, the sulfur of the abovementioned heterocycles maybe oxidized to S═O or S(═O)₂;and where the moiety is fused to the skeleton via two adjacent carbonatoms.

The compounds of the formula I according to the invention where R⁹=IIaare referred to as compounds of the formula Ia, and compounds of theformula I where R⁹=IIb are referred to as Ib.

Preference is given to the compounds of the formula I, where

-   R¹¹ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, hydroxyl,    C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;

Preference is likewise given to the compounds of the formula Ia.

With respect to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, in each case alone or in combination:

-   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;-   Y together with the two carbons to which it is attached forms a    saturated, partially saturated or unsaturated 5- or 6-membered    heterocycle which contains one or two identical or different    heteroatoms selected from the following group: oxygen, sulfur or    nitrogen;-   R¹,R² are hydrogen or C₁–C₆-alkyl;-   R³ is halogen, C₁–C₆-alkyl or C₁–C₆-alkoxy;-   R⁴ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,    C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, aminosulfonyl,    N-(C₁–C₆-alkyl)aminosulfonyl, N,N-di(C₁–C₆-alkyl)aminosulfonyl,    N-(C₁–C₆-alkylsulfonyl)amino, N-(C₁–C₆-haloalkylsulfonyl)amino,    N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino or    N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino;-    in particular nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,    C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl;-   R⁵ is hydrogen;-   R⁶,R⁷ are hydrogen or C₁–C₆-alkyl;-   R⁸ is C₁–C₆-alkyl, C₁–C₆-alkylcarbonyl or C₁–C₆-alkylsulfonyl;-   l is 0, 1 or 2;-   R⁹ is a radical IIa

where

-   R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴ or N-bonded    heterocyclyl, where the heterocyclyl radical may be partially or    fully halogenated and/or may carry one to three of the following    radicals:-    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or    C₁–C₄-haloalkoxy;-   R¹¹ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl or C₃–C₆-cycloalkyl;-   R¹² is hydrogen, C₁–C₆-alkyl or C₁–C₆-haloalkyl;-   R¹³ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl,    C₁–C₆-alkylcarbonyl, C₂–C₆-alkenylcarbonyl,    C₃–C₆-cycloalkylcarbonyl, C₁–C₆-alkoxycarbonyl,    C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl,    C₁–C₆-alkylthiocarbonyl, C₁–C₆-alkylaminocarbonyl,    C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl,    N,N-di(C₁–C₆-alkyl)aminocarbonyl,    N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,    N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,    N-(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,    N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl    N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,    di(C₁–C₆-alkyl)aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl,    C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl    or N,N-di(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, where the    abovementioned alkyl, cycloalkyl and alkoxy radicals may be    partially or fully halogenated and/or may carry one to three of the    following groups:-    cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,    C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, di(C₁–C₄-alkyl)aminocarbonyl,    C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;-    is phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,    heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,    heterocyclylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl,    heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl,    heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,    phenyl-C₂–C₆-alkenylcarbonyl or heterocyclyl-C₂–C₆-alkenylcarbonyl,    where the phenyl and the heterocyclyl radical of the 14    lastmentioned substituents may be partially or fully halogenated    and/or may carry one to three of the following radicals:-    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy,    C₁–C₄-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where the    two lastmentioned substituents for their part may be partially or    fully halogenated and/or may carry one to three of the following    radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy    or C₁–C₄-haloalkoxy;-   R¹⁴ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,    C₃–C₆-cycloalkyl, C₁–C₆-alkoxy or di(C₁–C₆-haloalkyl)amino, where    the abovementioned alkyl, cycloalkyl and alkoxy radicals may be    partially or fully halogenated and/or may carry one to three of the    following groups:-    cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,    C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, di(C₁–C₄-alkyl)aminocarbonyl,    C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;-    is phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,    heterocyclyl-C₁–C₆-alkyl, phenoxy, heterocyclyloxy, where the phenyl    and the heterocyclyl radical of the lastmentioned substituents may    be partially or fully halogenated and/or may carry one to three of    the following radicals:-    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or    C₁–C₄-haloalkoxy.

Particular preference is given to compounds of the formula I where thevariables have the following meanings, either alone or in combination:

-   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷ or a bond;-   Y together with the two carbons to which it is attached forms the    following heterocycles:-    (in the embodiments of the heterocycles below, the upper undulating    line represents in each case the link to the hydrocarbon which    carries the radicals R¹ and R², and the lower undulating line    represents the link to the meta-carbon of the benzoyl moiety).

where the sulfur of the abovementioned heterocycles may be oxidized toS═O or S(═O)₂;in particular, Y together with the two carbons to which it is attachedforms the following heterocycles:

-   R¹,R² are hydrogen;-   R³ is C₁–C₆-alkyl, such as methyl, ethyl or n-propyl;-    in particular methyl;-   R⁴ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylthio or C₁–C₆-alkylsulfonyl;-    in particular nitro, halogen, such as fluorine, chlorine or    bromine, C₁–C₆-haloalkyl such as trifluoromethyl, C₁–C₆-alkylthio,    such as methylthio or ethylthio, or C₁–C₆-alkylsulfonyl, such as    methylsulfonyl or ethylsulfonyl;-    particularly preferably nitro, chlorine, trifluoromethyl,    methylthio or methylsulfonyl;-   R⁵ is hydrogen;-   R⁶,R⁷ are hydrogen or C₁–C₆-alkyl, such as methyl or ethyl;-    in particular hydrogen or methyl;-   l is 0, 1 or 2;-    in particular 0 or 1;-   R⁹ is a radical IIa

where

-   R¹⁰ is hydroxyl;-   R¹¹ is C₁–C₆-alkyl, such as methyl, ethyl, n-propyl, 1-methylethyl,    n-butyl, 2-methylpropyl or 1,1-dimethylethyl or cyclopropyl;-    in particular methyl or ethyl;-    likewise particularly preferred cyclopropyl;-   R¹² is hydrogen or C₁–C₆-alkyl, such as methyl, ethyl, n-propyl or    1-methylethyl;-    in particular hydrogen or methyl.

Very particular preference is given to the compounds Ia where

-   X is oxygen, sulfur, S(═O)₂, CH₂ or a bond;-   Y together with the two carbons to which it is attached forms the    following heterocycles:

-   R¹,R² are hydrogen;-   R³ is C₁–C₄-alkyl;-   R⁴ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylthio or C₁–C₆-alkylsulfonyl;-   R⁵ is hydrogen or C₁–C₆-alkyl;-   l is 0, 1 or 2;-   R⁹ is a radical IIa;-   R¹⁰ is hydroxyl;-   R¹¹ is hydrogen, C₁–C₆-alkyl or cyclopropyl;-    in particular C₁–C₆-alkyl;-   R¹² is hydrogen, C₁–C₆-alkyl or C₁–C₆-haloalkyl.

Very particular preference is also given to the compounds Ia where X isoxygen, sulfur or a bond.

Very particular preference is also given to the compounds Ia where

-   Y together with the two carbons to which it is attached forms a    heterocycle selected from the following group: dihydropyrazolediyl,    dihydroisoxazolediyl, pyrazolediyl, isoxazolediyl or pyrimidinediyl.

Most preferably, Y together with the two carbons to which it is attachedforms the following heterocycles:

Very particular preference is also given to the compounds of the formulaI where

-   R¹, R² are hydrogen;-   R³ is C₁–C₆-alkyl;-   R⁴ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylthio or C₁–C₆-akylsulfonyl;-    in particular halogen, C₁–C₆-alkoxy, C₁–C₆-alkylthio or    C₁–C₆-alkylsulfonyl;-   R⁵ is hydrogen;-   l is 0 oder 1.

Very particular preference is also given to the compounds of the formulaI where

-   R¹⁰ is hydroxyl or phenylcarbonyloxy which may be unsubstituted or    partially or fully halogenated and/or may carry one to three of the    following radicals:-    nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or    C₁–C₄-haloalkoxy;-    in particular hydroxyl;-   R¹¹ is C₁–C₆-alkyl or C₃–C₆-cycloalkyl;-    in particular C₁–C₆-alkyl or-    also in particular cyclopropyl;-   R¹² is hydrogen or C₁–C₆-alkyl;-    in particular hydrogen.

Very particular preference is also given to the compounds of the formulaIa1 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0, meaning of the heterocycleaccording to structural formula), most particularly to compounds Ia1.nwhere the variables X, R⁴, R¹⁰ and R¹¹ are as defined in Table 1.

The radical definitions of R¹ to R¹², X, Y and l given above and themeaning of the fused heterocycle are of particular importance for thecompounds according to the invention, not only in combination with oneanother, but also taken on their own. (For reasons of clarity, in theformulae Ia1, Ia2 . . . , the meaning of the fused heterocycle is ineach case as given in the corresponding structural formula.)

TABLE 1 n X R⁴ R¹⁰ R¹¹ 1 bond F OH CH₃ 2 bond Cl OH CH₃ 3 bond Br OH CH₃4 bond NO₂ OH CH₃ 5 bond SCH₃ OH CH₃ 6 bond SO₂CH₃ OH CH₃ 7 bondSO₂CH₂CH₃ OH CH₃ 8 bond CH₃ OH CH₃ 9 bond CF₃ OH CH₃ 10 bond OCHF₂ OHCH₃ 11 CH₂ F OH CH₃ 12 CH₂ Cl OH CH₃ 13 CH₂ Br OH CH₃ 14 CH₂ NO₂ OH CH₃15 CH₂ SCH₃ OH CH₃ 16 CH₂ SO₂CH₃ OH CH₃ 17 CH₂ SO₂CH₂CH₃ OH CH₃ 18 CH₂CH₃ OH CH₃ 19 CH₂ CF₃ OH CH₃ 20 CH₂ OCHF₂ OH CH₃ 21 O F OH CH₃ 22 O ClOH CH₃ 23 O Br OH CH₃ 24 O NO₂ OH CH₃ 25 O SCH₃ OH CH₃ 26 O SO₂CH₃ OHCH₃ 27 O SO₂CH₂CH₃ OH CH₃ 28 O CH₃ OH CH₃ 29 O CF₃ OH CH₃ 30 O OCHF₂ OHCH₃ 31 S F OH CH₃ 32 S Cl OH CH₃ 33 S Br OH CH₃ 34 S NO₂ OH CH₃ 35 SSCH₃ OH CH₃ 36 S SO₂CH₃ OH CH₃ 37 S SO₂CH₂CH₃ OH CH₃ 38 S CH₃ OH CH₃ 39S CF₃ OH CH₃ 40 S OCHF₂ OH CH₃ 41 SO₂ F OH CH₃ 42 SO₂ Cl OH CH₃ 43 SO₂Br OH CH₃ 44 SO₂ NO₂ OH CH₃ 45 SO₂ SCH₃ OH CH₃ 46 SO₂ SO₂CH₃ OH CH₃ 47SO₂ SO₂CH₂CH₃ OH CH₃ 48 SO₂ CH₃ OH CH₃ 49 SO₂ CF₃ OH CH₃ 50 SO₂ OCHF₂ OHCH₃ 51 bond F OH CH₂CH₃ 52 bond Cl OH CH₂CH₃ 53 bond Br OH CH₂CH₃ 54bond NO₂ OH CH₂CH₃ 55 bond SCH₃ OH CH₂CH₃ 56 bond SO₂CH₃ OH CH₂CH₃ 57bond SO₂CH₂CH₃ OH CH₂CH₃ 58 bond CH₃ OH CH₂CH₃ 59 bond CF₃ OH CH₂CH₃ 60bond OCHF₂ OH CH₂CH₃ 61 CH₂ F OH CH₂CH₃ 62 CH₂ Cl OH CH₂CH₃ 63 CH₂ Br OHCH₂CH₃ 64 CH₂ NO₂ OH CH₂CH₃ 65 CH₂ SCH₃ OH CH₂CH₃ 66 CH₂ SO₂CH₃ OHCH₂CH₃ 67 CH₂ SO₂CH₂CH₃ OH CH₂CH₃ 68 CH₂ CH₃ OH CH₂CH₃ 69 CH₂ CF₃ OHCH₂CH₃ 70 CH₂ OCHF₂ OH CH₂CH₃ 71 O F OH CH₂CH₃ 72 O Cl OH CH₂CH₃ 73 O BrOH CH₂CH₃ 74 O NO₂ OH CH₂CH₃ 75 O SCH₃ OH CH₂CH₃ 76 O SO₂CH₃ OH CH₂CH₃77 O SO₂CH₂CH₃ OH CH₂CH₃ 78 O CH₃ OH CH₂CH₃ 79 O CF₃ OH CH₂CH₃ 80 OOCHF₂ OH CH₂CH₃ 81 S F OH CH₂CH₃ 82 S Cl OH CH₂CH₃ 83 S Br OH CH₂CH₃ 84S NO₂ OH CH₂CH₃ 85 S SCH₃ OH CH₂CH₃ 86 S SO₂CH₃ OH CH₂CH₃ 87 S SO₂CH₂CH₃OH CH₂CH₃ 88 S CH₃ OH CH₂CH₃ 89 S CF₃ OH CH₂CH₃ 90 S OCHF₂ OH CH₂CH₃ 91SO₂ F OH CH₂CH₃ 92 SO₂ Cl OH CH₂CH₃ 93 SO₂ Br OH CH₂CH₃ 94 SO₂ NO₂ OHCH₂CH₃ 95 SO₂ SCH₃ OH CH₂CH₃ 96 SO₂ SO₂CH₃ OH CH₂CH₃ 97 SO₂ SO₂CH₂CH₃ OHCH₂CH₃ 98 SO₂ CH₃ OH CH₂CH₃ 99 SO₂ CF₃ OH CH₂CH₃ 100 SO₂ OCHF₂ OH CH₂CH₃101 bond F OCOC₆H₅ CH₃ 102 bond Cl OCOC₆H₅ CH₃ 103 bond Br OCOC₆H₅ CH₃104 bond NO₂ OCOC₆H₅ CH₃ 105 bond SCH₃ OCOC₆H₅ CH₃ 106 bond SO₂CH₃OCOC₆H₅ CH₃ 107 bond SO₂CH₂CH₃ OCOC₆H₅ CH₃ 108 bond CH₃ OCOC₆H₅ CH₃ 109bond CF₃ OCOC₆H₅ CH₃ 110 bond OCHF₂ OCOC₆H₅ CH₃ 111 CH₂ F OCOC₆H₅ CH₃112 CH₂ Cl OCOC₆H₅ CH₃ 113 CH₂ Br OCOC₆H₅ CH₃ 114 CH₂ NO₂ OCOC₆H₅ CH₃115 CH₂ SCH₃ OCOC₆H₅ CH₃ 116 CH₂ SO₂CH₃ OCOC₆H₅ CH₃ 117 CH₂ SO₂CH₂CH₃OCOC₆H₅ CH₃ 118 CH₂ CH₃ OCOC₆H₅ CH₃ 119 CH₂ CF₃ OCOC₆H₅ CH₃ 120 CH₂OCHF₂ OCOC₆H₅ CH₃ 121 O F OCOC₆H₅ CH₃ 122 O Cl OCOC₆H₅ CH₃ 123 O BrOCOC₆H₅ CH₃ 124 O NO₂ OCOC₆H₅ CH₃ 125 O SCH₃ OCOC₆H₅ CH₃ 126 O SO₂CH₃OCOC₆H₅ CH₃ 127 O SO₂CH₂CH₃ OCOC₆H₅ CH₃ 128 O CH₃ OCOC₆H₅ CH₃ 129 O CF₃OCOC₆H₅ CH₃ 130 O OCHF₂ OCOC₆H₅ CH₃ 131 S F OCOC₆H₅ CH₃ 132 S Cl OCOC₆H₅CH₃ 133 S Br OCOC₆H₅ CH₃ 134 S NO₂ OCOC₆H₅ CH₃ 135 S SCH₃ OCOC₆H₅ CH₃136 S SO₂CH₃ OCOC₆H₅ CH₃ 137 S SO₂CH₂CH₃ OCOC₆H₅ CH₃ 138 S CH₃ OCOC₆H₅CH₃ 139 S CF₃ OCOC₆H₅ CH₃ 140 S OCHF₂ OCOC₆H₅ CH₃ 141 SO₂ F OCOC₆H₅ CH₃142 SO₂ Cl OCOC₆H₅ CH₃ 143 SO₂ Br OCOC₆H₅ CH₃ 144 SO₂ NO₂ OCOC₆H₅ CH₃145 SO₂ SCH₃ OCOC₆H₅ CH₃ 146 SO₂ SO₂CH₃ OCOC₆H₅ CH₃ 147 SO₂ SO₂CH₂CH₃OCOC₆H₅ CH₃ 148 SO₂ CH₃ OCOC₆H₅ CH₃ 149 SO₂ CF₃ OCOC₆H₅ CH₃ 150 SO₂OCHF₂ OCOC₆H₅ CH₃ 151 bond F OCOC₆H₅ CH₂CH₃ 152 bond Cl OCOC₆H₅ CH₂CH₃153 bond Br OCOC₆H₅ CH₂CH₃ 154 bond NO₂ OCOC₆H₅ CH₂CH₃ 155 bond SCH₃OCOC₆H₅ CH₂CH₃ 156 bond SO₂CH₃ OCOC₆H₅ CH₂CH₃ 157 bond SO₂CH₂CH₃ OCOC₆H₅CH₂CH₃ 158 bond CH₃ OCOC₆H₅ CH₂CH₃ 159 bond CF₃ OCOC₆H₅ CH₂CH₃ 160 bondOCHF₂ OCOC₆H₅ CH₂CH₃ 161 CH₂ F OCOC₆H₅ CH₂CH₃ 162 CH₂ Cl OCOC₆H₅ CH₂CH₃163 CH₂ Br OCOC₆H₅ CH₂CH₃ 164 CH₂ NO₂ OCOC₆H₅ CH₂CH₃ 165 CH₂ SCH₃OCOC₆H₅ CH₂CH₃ 166 CH₂ SO₂CH₃ OCOC₆H₅ CH₂CH₃ 167 CH₂ SO₂CH₂CH₃ OCOC₆H₅CH₂CH₃ 168 CH₂ CH₃ OCOC₆H₅ CH₂CH₃ 169 CH₂ CF₃ OCOC₆H₅ CH₂CH₃ 170 CH₂OCHF₂ OCOC₆H₅ CH₂CH₃ 171 O F OCOC₆H₅ CH₂CH₃ 172 O Cl OCOC₆H₅ CH₂CH₃ 173O Br OCOC₆H₅ CH₂CH₃ 174 O NO₂ OCOC₆H₅ CH₂CH₃ 175 O SCH₃ OCOC₆H₅ CH₂CH₃176 O SO₂CH₃ OCOC₆H₅ CH₂CH₃ 177 O SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃ 178 O CH₃OCOC₆H₅ CH₂CH₃ 179 O CF₃ OCOC₆H₅ CH₂CH₃ 180 O OCHF₂ OCOC₆H₅ CH₂CH₃ 181 SF OCOC₆H₅ CH₂CH₃ 182 S Cl OCOC₆H₅ CH₂CH₃ 183 S Br OCOC₆H₅ CH₂CH₃ 184 SNO₂ OCOC₆H₅ CH₂CH₃ 185 S SCH₃ OCOC₆H₅ CH₂CH₃ 186 S SO₂CH₃ OCOC₆H₅ CH₂CH₃187 S SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃ 188 S CH₃ OCOC₆H₅ CH₂CH₃ 189 S CF₃OCOC₆H₅ CH₂CH₃ 190 S OCHF₂ OCOC₆H₅ CH₂CH₃ 191 SO₂ F OCOC₆H₅ CH₂CH₃ 192SO₂ Cl OCOC₆H₅ CH₂CH₃ 193 SO₂ Br OCOC₆H₅ CH₂CH₃ 194 SO₂ NO₂ OCOC₆H₅CH₂CH₃ 195 SO₂ SCH₃ OCOC₆H₅ CH₂CH₃ 196 SO₂ SO₂CH₃ OCOC₆H₅ CH₂CH₃ 197 SO₂SO₂CH₂CH₃ OCOC₆H₅ CH₂CH₃ 198 SO₂ CH₃ OCOC₆H₅ CH₂CH₃ 199 SO₂ CF₃ OCOC₆H₅CH₂CH₃ 200 SO₂ OCHF₂ OCOC₆H₅ CH₂CH₃ 201 bond F OCOC(CH₃)₃ CH₃ 202 bondCl OCOC(CH₃)₃ CH₃ 203 bond Br OCOC(CH₃)₃ CH₃ 204 bond NO₂ OCOC(CH₃)₃ CH₃205 bond SCH₃ OCOC(CH₃)₃ CH₃ 206 bond SO₂CH₃ OCOC(CH₃)₃ CH₃ 207 bondSO₂CH₂CH₃ OCOC(CH₃)₃ CH₃ 208 bond CH₃ OCOC(CH₃)₃ CH₃ 209 bond CF₃OCOC(CH₃)₃ CH₃ 210 bond OCHF₂ OCOC(CH₃)₃ CH₃ 211 CH₂ F OCOC(CH₃)₃ CH₃212 CH₂ Cl OCOC(CH₃)₃ CH₃ 213 CH₂ Br OCOC(CH₃)₃ CH₃ 214 CH₂ NO₂OCOC(CH₃)₃ CH₃ 215 CH₂ SCH₃ OCOC(CH₃)₃ CH₃ 216 CH₂ SO₂CH₃ OCOC(CH₃)₃ CH₃217 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃ 218 CH₂ CH₃ OCOC(CH₃)₃ CH₃ 219 CH₂ CF₃OCOC(CH₃)₃ CH₃ 220 CH₂ OCHF₂ OCOC(CH₃)₃ CH₃ 221 O F OCOC(CH₃)₃ CH₃ 222 OCl OCOC(CH₃)₃ CH₃ 223 O Br OCOC(CH₃)₃ CH₃ 224 O NO₂ OCOC(CH₃)₃ CH₃ 225 OSCH₃ OCOC(CH₃)₃ CH₃ 226 O SO₂CH₃ OCOC(CH₃)₃ CH₃ 227 O SO₂CH₂CH₃OCOC(CH₃)₃ CH₃ 228 O CH₃ OCOC(CH₃)₃ CH₃ 229 O CF₃ OCOC(CH₃)₃ CH₃ 230 OOCHF₂ OCOC(CH₃)₃ CH₃ 231 S F OCOC(CH₃)₃ CH₃ 232 S Cl OCOC(CH₃)₃ CH₃ 233S Br OCOC(CH₃)₃ CH₃ 234 S NO₂ OCOC(CH₃)₃ CH₃ 235 S SCH₃ OCOC(CH₃)₃ CH₃236 S SO₂CH₃ OCOC(CH₃)₃ CH₃ 237 S SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃ 238 S CH₃OCOC(CH₃)₃ CH₃ 239 S CF₃ OCOC(CH₃)₃ CH₃ 240 S OCHF₂ OCOC(CH₃)₃ CH₃ 241SO₂ F OCOC(CH₃)₃ CH₃ 242 SO₂ Cl OCOC(CH₃)₃ CH₃ 243 SO₂ Br OCOC(CH₃)₃ CH₃244 SO₂ NO₂ OCOC(CH₃)₃ CH₃ 245 SO₂ SCH₃ OCOC(CH₃)₃ CH₃ 246 SO₂ SO₂CH₃OCOC(CH₃)₃ CH₃ 247 SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₃ 248 SO₂ CH₃ OCOC(CH₃)₃CH₃ 249 SO₂ CF₃ OCOC(CH₃)₃ CH₃ 250 SO₂ OCHF₂ OCOC(CH₃)₃ CH₃ 251 bond FOCOC(CH₃)₃ CH₂CH₃ 252 bond Cl OCOC(CH₃)₃ CH₂CH₃ 253 bond Br OCOC(CH₃)₃CH₂CH₃ 254 bond NO₂ OCOC(CH₃)₃ CH₂CH₃ 255 bond SCH₃ OCOC(CH₃)₃ CH₂CH₃256 bond SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 257 bond SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃258 bond CH₃ OCOC(CH₃)₃ CH₂CH₃ 259 bond CF₃ OCOC(CH₃)₃ CH₂CH₃ 260 bondOCHF₂ OCOC(CH₃)₃ CH₂CH₃ 261 CH₂ F OCOC(CH₃)₃ CH₂CH₃ 262 CH₂ ClOCOC(CH₃)₃ CH₂CH₃ 263 CH₂ Br OCOC(CH₃)₃ CH₂CH₃ 264 CH₂ NO₂ OCOC(CH₃)₃CH₂CH₃ 265 CH₂ SCH₃ OCOC(CH₃)₃ CH₂CH₃ 266 CH₂ SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃267 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 268 CH₂ CH₃ OCOC(CH₃)₃ CH₂CH₃ 269CH₂ CF₃ OCOC(CH₃)₃ CH₂CH₃ 270 CH₂ OCHF₂ OCOC(CH₃)₃ CH₂CH₃ 271 O FOCOC(CH₃)₃ CH₂CH₃ 272 O Cl OCOC(CH₃)₃ CH₂CH₃ 273 O Br OCOC(CH₃)₃ CH₂CH₃274 O NO₂ OCOC(CH₃)₃ CH₂CH₃ 275 O SCH₃ OCOC(CH₃)₃ CH₂CH₃ 276 O SO₂CH₃OCOC(CH₃)₃ CH₂CH₃ 277 O SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 278 O CH₃ OCOC(CH₃)₃CH₂CH₃ 279 O CF₃ OCOC(CH₃)₃ CH₂CH₃ 280 O OCHF₂ OCOC(CH₃)₃ CH₂CH₃ 281 S FOCOC(CH₃)₃ CH₂CH₃ 282 S Cl OCOC(CH₃)₃ CH₂CH₃ 283 S Br OCOC(CH₃)₃ CH₂CH₃284 S NO₂ OCOC(CH₃)₃ CH₂CH₃ 285 S SCH₃ OCOC(CH₃)₃ CH₂CH₃ 286 S SO₂CH₃OCOC(CH₃)₃ CH₂CH₃ 287 S SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 288 S CH₃ OCOC(CH₃)₃CH₂CH₃ 289 S CF₃ OCOC(CH₃)₃ CH₂CH₃ 290 S OCHF₂ OCOC(CH₃)₃ CH₂CH₃ 291 SO₂F OCOC(CH₃)₃ CH₂CH₃ 292 SO₂ Cl OCOC(CH₃)₃ CH₂CH₃ 293 SO₂ Br OCOC(CH₃)₃CH₂CH₃ 294 SO₂ NO₂ OCOC(CH₃)₃ CH₂CH₃ 295 SO₂ SCH₃ OCOC(CH₃)₃ CH₂CH₃ 296SO₂ SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 297 SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 298 SO₂CH₃ OCOC(CH₃)₃ CH₂CH₃ 299 SO₂ CF₃ OCOC(CH₃)₃ CH₂CH₃ 300 SO₂ OCHF₂OCOC(CH₃)₃ CH₂CH₃ 301 bond F OCOSCH₃ CH₃ 302 bond Cl OCOSCH₃ CH₃ 303bond Br OCOSCH₃ CH₃ 304 bond NO₂ OCOSCH₃ CH₃ 305 bond SCH₃ OCOSCH₃ CH₃306 bond SO₂CH₃ OCOSCH₃ CH₃ 307 bond SO₂CH₂CH₃ OCOSCH₃ CH₃ 308 bond CH₃OCOSCH₃ CH₃ 309 bond CF₃ OCOSCH₃ CH₃ 310 bond OCHF₂ OCOSCH₃ CH₃ 311 CH₂F OCOSCH₃ CH₃ 312 CH₂ Cl OCOSCH₃ CH₃ 313 CH₂ Br OCOSCH₃ CH₃ 314 CH₂ NO₂OCOSCH₃ CH₃ 315 CH₂ SCH₃ OCOSCH₃ CH₃ 316 CH₂ SO₂CH₃ OCOSCH₃ CH₃ 317 CH₂SO₂CH₂CH₃ OCOSCH₃ CH₃ 318 CH₂ CH₃ OCOSCH₃ CH₃ 319 CH₂ CF₃ OCOSCH₃ CH₃320 CH₂ OCHF₂ OCOSCH₃ CH₃ 321 O F OCOSCH₃ CH₃ 322 O Cl OCOSCH₃ CH₃ 323 OBr OCOSCH₃ CH₃ 324 O NO₂ OCOSCH₃ CH₃ 325 O SCH₃ OCOSCH₃ CH₃ 326 O SO₂CH₃OCOSCH₃ CH₃ 327 O SO₂CH₂CH₃ OCOSCH₃ CH₃ 328 O CH₃ OCOSCH₃ CH₃ 329 O CF₃OCOSCH₃ CH₃ 330 O OCHF₂ OCOSCH₃ CH₃ 331 S F OCOSCH₃ CH₃ 332 S Cl OCOSCH₃CH₃ 333 S Br OCOSCH₃ CH₃ 334 S NO₂ OCOSCH₃ CH₃ 335 S SCH₃ OCOSCH₃ CH₃336 S SO₂CH₃ OCOSCH₃ CH₃ 337 S SO₂CH₂CH₃ OCOSCH₃ CH₃ 338 S CH₃ OCOSCH₃CH₃ 339 S CF₃ OCOSCH₃ CH₃ 340 S OCHF₂ OCOSCH₃ CH₃ 341 SO₂ F OCOSCH₃ CH₃342 SO₂ Cl OCOSCH₃ CH₃ 343 SO₂ Br OCOSCH₃ CH₃ 344 SO₂ NO₂ OCOSCH₃ CH₃345 SO₂ SCH₃ OCOSCH₃ CH₃ 346 SO₂ SO₂CH₃ OCOSCH₃ CH₃ 347 SO₂ SO₂CH₂CH₃OCOSCH₃ CH₃ 348 SO₂ CH₃ OCOSCH₃ CH₃ 349 SO₂ CF₃ OCOSCH₃ CH₃ 350 SO₂OCHF₂ OCOSCH₃ CH₃ 351 bond F OCOSCH₃ CH₂CH₃ 352 bond Cl OCOSCH₃ CH₂CH₃353 bond Br OCOSCH₃ CH₂CH₃ 354 bond NO₂ OCOSCH₃ CH₂CH₃ 355 bond SCH₃OCOSCH₃ CH₂CH₃ 356 bond SO₂CH₃ OCOSCH₃ CH₂CH₃ 357 bond SO₂CH₂CH₃ OCOSCH₃CH₂CH₃ 358 bond CH₃ OCOSCH₃ CH₂CH₃ 359 bond CF₃ OCOSCH₃ CH₂CH₃ 360 bondOCHF₂ OCOSCH₃ CH₂CH₃ 361 CH₂ F OCOSCH₃ CH₂CH₃ 362 CH₂ Cl OCOSCH₃ CH₂CH₃363 CH₂ Br OCOSCH₃ CH₂CH₃ 364 CH₂ NO₂ OCOSCH₃ CH₂CH₃ 365 CH₂ SCH₃OCOSCH₃ CH₂CH₃ 366 CH₂ SO₂CH₃ OCOSCH₃ CH₂CH₃ 367 CH₂ SO₂CH₂CH₃ OCOSCH₃CH₂CH₃ 368 CH₂ CH₃ OCOSCH₃ CH₂CH₃ 369 CH₂ CF₃ OCOSCH₃ CH₂CH₃ 370 CH₂OCHF₂ OCOSCH₃ CH₂CH₃ 371 O F OCOSCH₃ CH₂CH₃ 372 O Cl OCOSCH₃ CH₂CH₃ 373O Br OCOSCH₃ CH₂CH₃ 374 O NO₂ OCOSCH₃ CH₂CH₃ 375 O SCH₃ OCOSCH₃ CH₂CH₃376 O SO₂CH₃ OCOSCH₃ CH₂CH₃ 377 O SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃ 378 O CH₃OCOSCH₃ CH₂CH₃ 379 O CF₃ OCOSCH₃ CH₂CH₃ 380 O OCHF₂ OCOSCH₃ CH₂CH₃ 381 SF OCOSCH₃ CH₂CH₃ 382 S Cl OCOSCH₃ CH₂CH₃ 383 S Br OCOSCH₃ CH₂CH₃ 384 SNO₂ OCOSCH₃ CH₂CH₃ 385 S SCH₃ OCOSCH₃ CH₂CH₃ 386 S SO₂CH₃ OCOSCH₃ CH₂CH₃387 S SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃ 388 S CH₃ OCOSCH₃ CH₂CH₃ 389 S CF₃OCOSCH₃ CH₂CH₃ 390 S OCHF₂ OCOSCH₃ CH₂CH₃ 391 SO₂ F OCOSCH₃ CH₂CH₃ 392SO₂ Cl OCOSCH₃ CH₂CH₃ 393 SO₂ Br OCOSCH₃ CH₂CH₃ 394 SO₂ NO₂ OCOSCH₃CH₂CH₃ 395 SO₂ SCH₃ OCOSCH₃ CH₂CH₃ 396 SO₂ SO₂CH₃ OCOSCH₃ CH₂CH₃ 397 SO₂SO₂CH₂CH₃ OCOSCH₃ CH₂CH₃ 398 SO₂ CH₃ OCOSCH₃ CH₂CH₃ 399 SO₂ CF₃ OCOSCH₃CH₂CH₃ 400 SO₂ OCHF₂ OCOSCH₃ CH₂CH₃ 401 bond F OCH₃ CH₃ 402 bond Cl OCH₃CH₃ 403 bond Br OCH₃ CH₃ 404 bond NO₂ OCH₃ CH₃ 405 bond SCH₃ OCH₃ CH₃406 bond SO₂CH₃ OCH₃ CH₃ 407 bond SO₂CH₂CH₃ OCH₃ CH₃ 408 bond CH₃ OCH₃CH₃ 409 bond CF₃ OCH₃ CH₃ 410 bond OCHF₂ OCH₃ CH₃ 411 CH₂ F OCH₃ CH₃ 412CH₂ Cl OCH₃ CH₃ 413 CH₂ Br OCH₃ CH₃ 414 CH₂ NO₂ OCH₃ CH₃ 415 CH₂ SCH₃OCH₃ CH₃ 416 CH₂ SO₂CH₃ OCH₃ CH₃ 417 CH₂ SO₂CH₂CH₃ OCH₃ CH₃ 418 CH₂ CH₃OCH₃ CH₃ 419 CH₂ CF₃ OCH₃ CH₃ 420 CH₂ OCHF₂ OCH₃ CH₃ 421 O F OCH₃ CH₃422 O Cl OCH₃ CH₃ 423 O Br OCH₃ CH₃ 424 O NO₂ OCH₃ CH₃ 425 O SCH₃ OCH₃CH₃ 426 O SO₂CH₃ OCH₃ CH₃ 427 O SO₂CH₂CH₃ OCH₃ CH₃ 428 O CH₃ OCH₃ CH₃429 O CF₃ OCH₃ CH₃ 430 O OCHF₂ OCH₃ CH₃ 431 S F OCH₃ CH₃ 432 S Cl OCH₃CH₃ 433 S Br OCH₃ CH₃ 434 S NO₂ OCH₃ CH₃ 435 S SCH₃ OCH₃ CH₃ 436 SSO₂CH₃ OCH₃ CH₃ 437 S SO₂CH₂CH₃ OCH₃ CH₃ 438 S CH₃ OCH₃ CH₃ 439 S CF₃OCH₃ CH₃ 440 S OCHF₂ OCH₃ CH₃ 441 SO₂ F OCH₃ CH₃ 442 SO₂ Cl OCH₃ CH₃ 443SO₂ Br OCH₃ CH₃ 444 SO₂ NO₂ OCH₃ CH₃ 445 SO₂ SCH₃ OCH₃ CH₃ 446 SO₂SO₂CH₃ OCH₃ CH₃ 447 SO₂ SO₂CH₂CH₃ OCH₃ CH₃ 448 SO₂ CH₃ OCH₃ CH₃ 449 SO₂CF₃ OCH₃ CH₃ 450 SO₂ OCHF₂ OCH₃ CH₃ 451 bond F OCH₃ CH₂CH₃ 452 bond ClOCH₃ CH₂CH₃ 453 bond Br OCH₃ CH₂CH₃ 454 bond NO₂ OCH₃ CH₂CH₃ 455 bondSCH₃ OCH₃ CH₂CH₃ 456 bond SO₂CH₃ OCH₃ CH₂CH₃ 457 bond SO₂CH₂CH₃ OCH₃CH₂CH₃ 458 bond CH₃ OCH₃ CH₂CH₃ 459 bond CF₃ OCH₃ CH₂CH₃ 460 bond OCHF₂OCH₃ CH₂CH₃ 461 CH₂ F OCH₃ CH₂CH₃ 462 CH₂ Cl OCH₃ CH₂CH₃ 463 CH₂ Br OCH₃CH₂CH₃ 464 CH₂ NO₂ OCH₃ CH₂CH₃ 465 CH₂ SCH₃ OCH₃ CH₂CH₃ 466 CH₂ SO₂CH₃OCH₃ CH₂CH₃ 467 CH₂ SO₂CH₂CH₃ OCH₃ CH₂CH₃ 468 CH₂ CH₃ OCH₃ CH₂CH₃ 469CH₂ CF₃ OCH₃ CH₂CH₃ 470 CH₂ OCHF₂ OCH₃ CH₂CH₃ 471 O F OCH₃ CH₂CH₃ 472 OCl OCH₃ CH₂CH₃ 473 O Br OCH₃ CH₂CH₃ 474 O NO₂ OCH₃ CH₂CH₃ 475 O SCH₃OCH₃ CH₂CH₃ 476 O SO₂CH₃ OCH₃ CH₂CH₃ 477 O SO₂CH₂CH₃ OCH₃ CH₂CH₃ 478 OCH₃ OCH₃ CH₂CH₃ 479 O CF₃ OCH₃ CH₂CH₃ 480 O OCHF₂ OCH₃ CH₂CH₃ 481 S FOCH₃ CH₂CH₃ 482 S Cl OCH₃ CH₂CH₃ 483 S Br OCH₃ CH₂CH₃ 484 S NO₂ OCH₃CH₂CH₃ 485 S SCH₃ OCH₃ CH₂CH₃ 486 S SO₂CH₃ OCH₃ CH₂CH₃ 487 S SO₂CH₂CH₃OCH₃ CH₂CH₃ 488 S CH₃ OCH₃ CH₂CH₃ 489 S CF₃ OCH₃ CH₂CH₃ 490 S OCHF₂ OCH₃CH₂CH₃ 491 SO₂ F OCH₃ CH₂CH₃ 492 SO₂ Cl OCH₃ CH₂CH₃ 493 SO₂ Br OCH₃CH₂CH₃ 494 SO₂ NO₂ OCH₃ CH₂CH₃ 495 SO₂ SCH₃ OCH₃ CH₂CH₃ 496 SO₂ SO₂CH₃OCH₃ CH₂CH₃ 497 SO₂ SO₂CH₂CH₃ OCH₃ CH₂CH₃ 498 SO₂ CH₃ OCH₃ CH₂CH₃ 499SO₂ CF₃ OCH₃ CH₂CH₃ 500 SO₂ OCHF₂ OCH₃ CH₂CH₃ 501 bond F OCH(CH₃)₂ CH₃502 bond Cl OCH(CH₃)₂ CH₃ 503 bond Br OCH(CH₃)₂ CH₃ 504 bond NO₂OCH(CH₃)₂ CH₃ 505 bond SCH₃ OCH(CH₃)₂ CH₃ 506 bond SO₂CH₃ OCH(CH₃)₂ CH₃507 bond SO₂CH₂CH₃ OCH(CH₃)₂ CH₃ 508 bond CH₃ OCH(CH₃)₂ CH₃ 509 bond CF₃OCH(CH₃)₂ CH₃ 510 bond OCHF₂ OCH(CH₃)₂ CH₃ 511 CH₂ F OCH(CH₃)₂ CH₃ 512CH₂ Cl OCH(CH₃)₂ CH₃ 513 CH₂ Br OCH(CH₃)₂ CH₃ 514 CH₂ NO₂ OCH(CH₃)₂ CH₃515 CH₂ SCH₃ OCH(CH₃)₂ CH₃ 516 CH₂ SO₂CH₃ OCH(CH₃)₂ CH₃ 517 CH₂SO₂CH₂CH₃ OCH(CH₃)₂ CH₃ 518 CH₂ CH₃ OCH(CH₃)₂ CH₃ 519 CH₂ CF₃ OCH(CH₃)₂CH₃ 520 CH₂ OCHF₂ OCH(CH₃)₂ CH₃ 521 O F OCH(CH₃)₂ CH₃ 522 O Cl OCH(CH₃)₂CH₃ 523 O Br OCH(CH₃)₂ CH₃ 524 O NO₂ OCH(CH₃)₂ CH₃ 525 O SCH₃ OCH(CH₃)₂CH₃ 526 O SO₂CH₃ OCH(CH₃)₂ CH₃ 527 O SO₂CH₂CH₃ OCH(CH₃)₂ CH₃ 528 O CH₃OCH(CH₃)₂ CH₃ 529 O CF₃ OCH(CH₃)₂ CH₃ 530 O OCHF₂ OCH(CH₃)₂ CH₃ 531 S FOCH(CH₃)₂ CH₃ 532 S Cl OCH(CH₃)₂ CH₃ 533 S Br OCH(CH₃)₂ CH₃ 534 S NO₂OCH(CH₃)₂ CH₃ 535 S SCH₃ OCH(CH₃)₂ CH₃ 536 S SO₂CH₃ OCH(CH₃)₂ CH₃ 537 SSO₂CH₂CH₃ OCH(CH₃)₂ CH₃ 538 S CH₃ OCH(CH₃)₂ CH₃ 539 S CF₃ OCH(CH₃)₂ CH₃540 S OCHF₂ OCH(CH₃)₂ CH₃ 541 SO₂ F OCH(CH₃)₂ CH₃ 542 SO₂ Cl OCH(CH₃)₂CH₃ 543 SO₂ Br OCH(CH₃)₂ CH₃ 544 SO₂ NO₂ OCH(CH₃)₂ CH₃ 545 SO₂ SCH₃OCH(CH₃)₂ CH₃ 546 SO₂ SO₂CH₃ OCH(CH₃)₂ CH₃ 547 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂CH₃ 548 SO₂ CH₃ OCH(CH₃)₂ CH₃ 549 SO₂ CF₃ OCH(CH₃)₂ CH₃ 550 SO₂ OCHF₂OCH(CH₃)₂ CH₃ 551 bond F OCH(CH₃)₂ CH₂CH₃ 552 bond Cl OCH(CH₃)₂ CH₂CH₃553 bond Br OCH(CH₃)₂ CH₂CH₃ 554 bond NO₂ OCH(CH₃)₂ CH₂CH₃ 555 bond SCH₃OCH(CH₃)₂ CH₂CH₃ 556 bond SO₂CH₃ OCH(CH₃)₂ CH₂CH₃ 557 bond SO₂CH₂CH₃OCH(CH₃)₂ CH₂CH₃ 558 bond CH₃ OCH(CH₃)₂ CH₂CH₃ 559 bond CF₃ OCH(CH₃)₂CH₂CH₃ 560 bond OCHF₂ OCH(CH₃)₂ CH₂CH₃ 561 CH₂ F OCH(CH₃)₂ CH₂CH₃ 562CH₂ Cl OCH(CH₃)₂ CH₂CH₃ 563 CH₂ Br OCH(CH₃)₂ CH₂CH₃ 564 CH₂ NO₂OCH(CH₃)₂ CH₂CH₃ 565 CH₂ SCH₃ OCH(CH₃)₂ CH₂CH₃ 566 CH₂ SO₂CH₃ OCH(CH₃)₂CH₂CH₃ 567 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃ 568 CH₂ CH₃ OCH(CH₃)₂ CH₂CH₃569 CH₂ CF₃ OCH(CH₃)₂ CH₂CH₃ 570 CH₂ OCHF₂ OCH(CH₃)₂ CH₂CH₃ 571 O FOCH(CH₃)₂ CH₂CH₃ 572 O Cl OCH(CH₃)₂ CH₂CH₃ 573 O Br OCH(CH₃)₂ CH₂CH₃ 574O NO₂ OCH(CH₃)₂ CH₂CH₃ 575 O SCH₃ OCH(CH₃)₂ CH₂CH₃ 576 O SO₂CH₃OCH(CH₃)₂ CH₂CH₃ 577 O SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃ 578 O CH₃ OCH(CH₃)₂CH₂CH₃ 579 O CF₃ OCH(CH₃)₂ CH₂CH₃ 580 O OCHF₂ OCH(CH₃)₂ CH₂CH₃ 581 S FOCH(CH₃)₂ CH₂CH₃ 582 S Cl OCH(CH₃)₂ CH₂CH₃ 583 S Br OCH(CH₃)₂ CH₂CH₃ 584S NO₂ OCH(CH₃)₂ CH₂CH₃ 585 S SCH₃ OCH(CH₃)₂ CH₂CH₃ 586 S SO₂CH₃OCH(CH₃)₂ CH₂CH₃ 587 S SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃ 588 S CH₃ OCH(CH₃)₂CH₂CH₃ 589 S CF₃ OCH(CH₃)₂ CH₂CH₃ 590 S OCHF₂ OCH(CH₃)₂ CH₂CH₃ 591 SO₂ FOCH(CH₃)₂ CH₂CH₃ 592 SO₂ Cl OCH(CH₃)₂ CH₂CH₃ 593 SO₂ Br OCH(CH₃)₂ CH₂CH₃594 SO₂ NO₂ OCH(CH₃)₂ CH₂CH₃ 595 SO₂ SCH₃ OCH(CH₃)₂ CH₂CH₃ 596 SO₂SO₂CH₃ OCH(CH₃)₂ CH₂CH₃ 597 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH₂CH₃ 598 SO₂ CH₃OCH(CH₃)₂ CH₂CH₃ 599 SO₂ CF₃ OCH(CH₃)₂ CH₂CH₃ 600 SO₂ OCHF₂ OCH(CH₃)₂CH₂CH₃ 601 bond F OCH₂C₆H₅ CH₃ 602 bond Cl OCH₂C₆H₅ CH₃ 603 bond BrOCH₂C₆H₅ CH₃ 604 bond NO₂ OCH₂C₆H₅ CH₃ 605 bond SCH₃ OCH₂C₆H₅ CH₃ 606bond SO₂CH₃ OCH₂C₆H₅ CH₃ 607 bond SO₂CH₂CH₃ OCH₂C₆H₅ CH₃ 608 bond CH₃OCH₂C₆H₅ CH₃ 609 bond CF₃ OCH₂C₆H₅ CH₃ 610 bond OCHF₂ OCH₂C₆H₅ CH₃ 611CH₂ F OCH₂C₆H₅ CH₃ 612 CH₂ Cl OCH₂C₆H₅ CH₃ 613 CH₂ Br OCH₂C₆H₅ CH₃ 614CH₂ NO₂ OCH₂C₆H₅ CH₃ 615 CH₂ SCH₃ OCH₂C₆H₅ CH₃ 616 CH₂ SO₂CH₃ OCH₂C₆H₅CH₃ 617 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₃ 618 CH₂ CH₃ OCH₂C₆H₅ CH₃ 619 CH₂ CF₃OCH₂C₆H₅ CH₃ 620 CH₂ OCHF₂ OCH₂C₆H₅ CH₃ 621 O F OCH₂C₆H₅ CH₃ 622 O ClOCH₂C₆H₅ CH₃ 623 O Br OCH₂C₆H₅ CH₃ 624 O NO₂ OCH₂C₆H₅ CH₃ 625 O SCH₃OCH₂C₆H₅ CH₃ 626 O SO₂CH₃ OCH₂C₆H₅ CH₃ 627 O SO₂CH₂CH₃ OCH₂C₆H₅ CH₃ 628O CH₃ OCH₂C₆H₅ CH₃ 629 O CF₃ OCH₂C₆H₅ CH₃ 630 O OCHF₂ OCH₂C₆H₅ CH₃ 631 SF OCH₂C₆H₅ CH₃ 632 S Cl OCH₂C₆H₅ CH₃ 633 S Br OCH₂C₆H₅ CH₃ 634 S NO₂OCH₂C₆H₅ CH₃ 635 S SCH₃ OCH₂C₆H₅ CH₃ 636 S SO₂CH₃ OCH₂C₆H₅ CH₃ 637 SSO₂CH₂CH₃ OCH₂C₆H₅ CH₃ 638 S CH₃ OCH₂C₆H₅ CH₃ 639 S CF₃ OCH₂C₆H₅ CH₃ 640S OCHF₂ OCH₂C₆H₅ CH₃ 641 SO₂ F OCH₂C₆H₅ CH₃ 642 SO₂ Cl OCH₂C₆H₅ CH₃ 643SO₂ Br OCH₂C₆H₅ CH₃ 644 SO₂ NO₂ OCH₂C₆H₅ CH₃ 645 SO₂ SCH₃ OCH₂C₆H₅ CH₃646 SO₂ SO₂CH₃ OCH₂C₆H₅ CH₃ 647 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₃ 648 SO₂ CH₃OCH₂C₆H₅ CH₃ 649 SO₂ CF₃ OCH₂C₆H₅ CH₃ 650 SO₂ OCHF₂ OCH₂C₆H₅ CH₃ 651bond F OCH₂C₆H₅ CH₂CH₃ 652 bond Cl OCH₂C₆H₅ CH₂CH₃ 653 bond Br OCH₂C₆H₅CH₂CH₃ 654 bond NO₂ OCH₂C₆H₅ CH₂CH₃ 655 bond SCH₃ OCH₂C₆H₅ CH₂CH₃ 656bond SO₂CH₃ OCH₂C₆H₅ CH₂CH₃ 657 bond SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃ 658 bondCH₃ OCH₂C₆H₅ CH₂CH₃ 659 bond CF₃ OCH₂C₆H₅ CH₂CH₃ 660 bond OCHF₂ OCH₂C₆H₅CH₂CH₃ 661 CH₂ F OCH₂C₆H₅ CH₂CH₃ 662 CH₂ Cl OCH₂C₆H₅ CH₂CH₃ 663 CH₂ BrOCH₂C₆H₅ CH₂CH₃ 664 CH₂ NO₂ OCH₂C₆H₅ CH₂CH₃ 665 CH₂ SCH₃ OCH₂C₆H₅ CH₂CH₃666 CH₂ SO₂CH₃ OCH₂C₆H₅ CH₂CH₃ 667 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃ 668 CH₂CH₃ OCH₂C₆H₅ CH₂CH₃ 669 CH₂ CF₃ OCH₂C₆H₅ CH₂CH₃ 670 CH₂ OCHF₂ OCH₂C₆H₅CH₂CH₃ 671 O F OCH₂C₆H₅ CH₂CH₃ 672 O Cl OCH₂C₆H₅ CH₂CH₃ 673 O BrOCH₂C₆H₅ CH₂CH₃ 674 O NO₂ OCH₂C₆H₅ CH₂CH₃ 675 O SCH₃ OCH₂C₆H₅ CH₂CH₃ 676O SO₂CH₃ OCH₂C₆H₅ CH₂CH₃ 677 O SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃ 678 O CH₃OCH₂C₆H₅ CH₂CH₃ 679 O CF₃ OCH₂C₆H₅ CH₂CH₃ 680 O OCHF₂ OCH₂C₆H₅ CH₂CH₃681 S F OCH₂C₆H₅ CH₂CH₃ 682 S Cl OCH₂C₆H₅ CH₂CH₃ 683 S Br OCH₂C₆H₅CH₂CH₃ 684 S NO₂ OCH₂C₆H₅ CH₂CH₃ 685 S SCH₃ OCH₂C₆H₅ CH₂CH₃ 686 S SO₂CH₃OCH₂C₆H₅ CH₂CH₃ 687 S SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃ 688 S CH₃ OCH₂C₆H₅CH₂CH₃ 689 S CF₃ OCH₂C₆H₅ CH₂CH₃ 690 S OCHF₂ OCH₂C₆H₅ CH₂CH₃ 691 SO₂ FOCH₂C₆H₅ CH₂CH₃ 692 SO₂ Cl OCH₂C₆H₅ CH₂CH₃ 693 SO₂ Br OCH₂C₆H₅ CH₂CH₃694 SO₂ NO₂ OCH₂C₆H₅ CH₂CH₃ 695 SO₂ SCH₃ OCH₂C₆H₅ CH₂CH₃ 696 SO₂ SO₂CH₃OCH₂C₆H₅ CH₂CH₃ 697 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH₂CH₃ 698 SO₂ CH₃ OCH₂C₆H₅CH₂CH₃ 699 SO₂ CF₃ OCH₂C₆H₅ CH₂CH₃ 700 SO₂ OCHF₂ OCH₂C₆H₅ CH₂CH₃ 701bond F OSO₂(4-CH₃—C₆H₄) CH₃ 702 bond Cl OSO₂(4-CH₃—C₆H₄) CH₃ 703 bond BrOSO₂(4-CH₃—C₆H₄) CH₃ 704 bond NO₂ OSO₂(4-CH₃—C₆H₄) CH₃ 705 bond SCH₃OSO₂(4-CH₃—C₆H₄) CH₃ 706 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 707 bondSO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 708 bond CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 709bond CF₃ OSO₂(4-CH₃—C₆H₄) CH₃ 710 bond OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃ 711CH₂ F OSO₂(4-CH₃—C₆H₄) CH₃ 712 CH₂ Cl OSO₂(4-CH₃—C₆H₄) CH₃ 713 CH₂ BrOSO₂(4-CH₃—C₆H₄) CH₃ 714 CH₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH₃ 715 CH₂ SCH₃OSO₂(4-CH₃—C₆H₄) CH₃ 716 CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 717 CH₂SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 718 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 719 CH₂CF₃ OSO₂(4-CH₃—C₆H₄) CH₃ 720 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃ 721 O FOSO₂(4-CH₃—C₆H₄) CH₃ 722 O Cl OSO₂(4-CH₃—C₆H₄) CH₃ 723 O BrOSO₂(4-CH₃—C₆H₄) CH₃ 724 O NO₂ OSO₂(4-CH₃—C₆H₄) CH₃ 725 O SCH₃OSO₂(4-CH₃—C₆H₄) CH₃ 726 O SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 727 O SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) CH₃ 728 O CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 729 O CF₃OSO₂(4-CH₃—C₆H₄) CH₃ 730 O OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃ 731 S FOSO₂(4-CH₃—C₆H₄) CH₃ 732 S Cl OSO₂(4-CH₃—C₆H₄) CH₃ 733 S BrOSO₂(4-CH₃—C₆H₄) CH₃ 734 S NO₂ OSO₂(4-CH₃—C₆H₄) CH₃ 735 S SCH₃OSO₂(4-CH₃—C₆H₄) CH₃ 736 S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 737 S SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) CH₃ 738 S CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 739 S CF₃OSO₂(4-CH₃—C₆H₄) CH₃ 740 S OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃ 741 SO₂ FOSO₂(4-CH₃—C₆H₄) CH₃ 742 SO₂ Cl OSO₂(4-CH₃—C₆H₄) CH₃ 743 SO₂ BrOSO₂(4-CH₃—C₆H₄) CH₃ 744 SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH₃ 745 SO₂ SCH₃OSO₂(4-CH₃—C₆H₄) CH₃ 746 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 747 SO₂SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 748 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₃ 749 SO₂CF₃ OSO₂(4-CH₃—C₆H₄) CH₃ 750 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₃ 751 bond FOSO₂(4-CH₃—C₆H₄) CH₂CH₃ 752 bond Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 753 bond BrOSO₂(4-CH₃—C₆H₄) CH₂CH₃ 754 bond NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 755 bondSCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 756 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 757bond SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 758 bond CH₃ OSO₂(4-CH₃—C₆H₄)CH₂CH₃ 759 bond CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 760 bond OCHF₂OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 761 CH₂ F OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 762 CH₂ ClOSO₂(4-CH₃—C₆H₄) CH₂CH₃ 763 CH₂ Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 764 CH₂ NO₂OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 765 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 766 CH₂SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 767 CH₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃768 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 769 CH₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃770 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 771 O F OSO₂(4-CH₃—C₆H₄) CH₂CH₃772 O Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 773 O Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 774 ONO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 775 O SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 776 OSO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 777 O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃778 O CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 779 O CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 780O OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 781 S F OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 782 S ClOSO₂(4-CH₃—C₆H₄) CH₂CH₃ 783 S Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 784 S NO₂OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 785 S SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 786 S SO₂CH₃OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 787 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 788 SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 789 S CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 790 SOCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 791 SO₂ F OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 792 SO₂Cl OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 793 SO₂ Br OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 794 SO₂NO₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 795 SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 796 SO₂SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 797 SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃798 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 799 SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH₂CH₃800 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) CH₂CH₃ 801 bond F SCH₃ CH₃ 802 bond ClSCH₃ CH₃ 803 bond Br SCH₃ CH₃ 804 bond NO₂ SCH₃ CH₃ 805 bond SCH₃ SCH₃CH₃ 806 bond SO₂CH₃ SCH₃ CH₃ 807 bond SO₂CH₂CH₃ SCH₃ CH₃ 808 bond CH₃SCH₃ CH₃ 809 bond CF₃ SCH₃ CH₃ 810 bond OCHF₂ SCH₃ CH₃ 811 CH₂ F SCH₃CH₃ 812 CH₂ Cl SCH₃ CH₃ 813 CH₂ Br SCH₃ CH₃ 814 CH₂ NO₂ SCH₃ CH₃ 815 CH₂SCH₃ SCH₃ CH₃ 816 CH₂ SO₂CH₃ SCH₃ CH₃ 817 CH₂ SO₂CH₂CH₃ SCH₃ CH₃ 818 CH₂CH₃ SCH₃ CH₃ 819 CH₂ CF₃ SCH₃ CH₃ 820 CH₂ OCHF₂ SCH₃ CH₃ 821 O F SCH₃CH₃ 822 O Cl SCH₃ CH₃ 823 O Br SCH₃ CH₃ 824 O NO₂ SCH₃ CH₃ 825 O SCH₃SCH₃ CH₃ 826 O SO₂CH₃ SCH₃ CH₃ 827 O SO₂CH₂CH₃ SCH₃ CH₃ 828 O CH₃ SCH₃CH₃ 829 O CF₃ SCH₃ CH₃ 830 O OCHF₂ SCH₃ CH₃ 831 S F SCH₃ CH₃ 832 S ClSCH₃ CH₃ 833 S Br SCH₃ CH₃ 834 S NO₂ SCH₃ CH₃ 835 S SCH₃ SCH₃ CH₃ 836 SSO₂CH₃ SCH₃ CH₃ 837 S SO₂CH₂CH₃ SCH₃ CH₃ 838 S CH₃ SCH₃ CH₃ 839 S CF₃SCH₃ CH₃ 840 S OCHF₂ SCH₃ CH₃ 841 SO₂ F SCH₃ CH₃ 842 SO₂ Cl SCH₃ CH₃ 843SO₂ Br SCH₃ CH₃ 844 SO₂ NO₂ SCH₃ CH₃ 845 SO₂ SCH₃ SCH₃ CH₃ 846 SO₂SO₂CH₃ SCH₃ CH₃ 847 SO₂ SO₂CH₂CH₃ SCH₃ CH₃ 848 SO₂ CH₃ SCH₃ CH₃ 849 SO₂CF₃ SCH₃ CH₃ 850 SO₂ OCHF₂ SCH₃ CH₃ 851 bond F SCH₃ CH₂CH₃ 852 bond ClSCH₃ CH₂CH₃ 853 bond Br SCH₃ CH₂CH₃ 854 bond NO₂ SCH₃ CH₂CH₃ 855 bondSCH₃ SCH₃ CH₂CH₃ 856 bond SO₂CH₃ SCH₃ CH₂CH₃ 857 bond SO₂CH₂CH₃ SCH₃CH₂CH₃ 858 bond CH₃ SCH₃ CH₂CH₃ 859 bond CF₃ SCH₃ CH₂CH₃ 860 bond OCHF₂SCH₃ CH₂CH₃ 861 CH₂ F SCH₃ CH₂CH₃ 862 CH₂ Cl SCH₃ CH₂CH₃ 863 CH₂ Br SCH₃CH₂CH₃ 864 CH₂ NO₂ SCH₃ CH₂CH₃ 865 CH₂ SCH₃ SCH₃ CH₂CH₃ 866 CH₂ SO₂CH₃SCH₃ CH₂CH₃ 867 CH₂ SO₂CH₂CH₃ SCH₃ CH₂CH₃ 868 CH₂ CH₃ SCH₃ CH₂CH₃ 869CH₂ CF₃ SCH₃ CH₂CH₃ 870 CH₂ OCHF₂ SCH₃ CH₂CH₃ 871 O F SCH₃ CH₂CH₃ 872 OCl SCH₃ CH₂CH₃ 873 O Br SCH₃ CH₂CH₃ 874 O NO₂ SCH₃ CH₂CH₃ 875 O SCH₃SCH₃ CH₂CH₃ 876 O SO₂CH₃ SCH₃ CH₂CH₃ 877 O SO₂CH₂CH₃ SCH₃ CH₂CH₃ 878 OCH₃ SCH₃ CH₂CH₃ 879 O CF₃ SCH₃ CH₂CH₃ 880 O OCHF₂ SCH₃ CH₂CH₃ 881 S FSCH₃ CH₂CH₃ 882 S Cl SCH₃ CH₂CH₃ 883 S Br SCH₃ CH₂CH₃ 884 S NO₂ SCH₃CH₂CH₃ 885 S SCH₃ SCH₃ CH₂CH₃ 886 S SO₂CH₃ SCH₃ CH₂CH₃ 887 S SO₂CH₂CH₃SCH₃ CH₂CH₃ 888 S CH₃ SCH₃ CH₂CH₃ 889 S CF₃ SCH₃ CH₂CH₃ 890 S OCHF₂ SCH₃CH₂CH₃ 891 SO₂ F SCH₃ CH₂CH₃ 892 SO₂ Cl SCH₃ CH₂CH₃ 893 SO₂ Br SCH₃CH₂CH₃ 894 SO₂ NO₂ SCH₃ CH₂CH₃ 895 SO₂ SCH₃ SCH₃ CH₂CH₃ 896 SO₂ SO₂CH₃SCH₃ CH₂CH₃ 897 SO₂ SO₂CH₂CH₃ SCH₃ CH₂CH₃ 898 SO₂ CH₃ SCH₃ CH₂CH₃ 899SO₂ CF₃ SCH₃ CH₂CH₃ 900 SO₂ OCHF₂ SCH₃ CH₂CH₃ 901 bond F Cl CH₃ 902 bondCl Cl CH₃ 903 bond Br Cl CH₃ 904 bond NO₂ Cl CH₃ 905 bond SCH₃ Cl CH₃906 bond SO₂CH₃ Cl CH₃ 907 bond SO₂CH₂CH₃ Cl CH₃ 908 bond CH₃ Cl CH₃ 909bond CF₃ Cl CH₃ 910 bond OCHF₂ Cl CH₃ 911 CH₂ F Cl CH₃ 912 CH₂ Cl Cl CH₃913 CH₂ Br Cl CH₃ 914 CH₂ NO₂ Cl CH₃ 915 CH₂ SCH₃ Cl CH₃ 916 CH₂ SO₂CH₃Cl CH₃ 917 CH₂ SO₂CH₂CH₃ Cl CH₃ 918 CH₂ CH₃ Cl CH₃ 919 CH₂ CF₃ Cl CH₃920 CH₂ OCHF₂ Cl CH₃ 921 O F Cl CH₃ 922 O Cl Cl CH₃ 923 O Br Cl CH₃ 924O NO₂ Cl CH₃ 925 O SCH₃ Cl CH₃ 926 O SO₂CH₃ Cl CH₃ 927 O SO₂CH₂CH₃ ClCH₃ 928 O CH₃ Cl CH₃ 929 O CF₃ Cl CH₃ 930 O OCHF₂ Cl CH₃ 931 S F Cl CH₃932 S Cl Cl CH₃ 933 S Br Cl CH₃ 934 S NO₂ Cl CH₃ 935 S SCH₃ Cl CH₃ 936 SSO₂CH₃ Cl CH₃ 937 S SO₂CH₂CH₃ Cl CH₃ 938 S CH₃ Cl CH₃ 939 S CF₃ Cl CH₃940 S OCHF₂ Cl CH₃ 941 SO₂ F Cl CH₃ 942 SO₂ Cl Cl CH₃ 943 SO₂ Br Cl CH₃944 SO₂ NO₂ Cl CH₃ 945 SO₂ SCH₃ Cl CH₃ 946 SO₂ SO₂CH₃ Cl CH₃ 947 SO₂SO₂CH₂CH₃ Cl CH₃ 948 SO₂ CH₃ Cl CH₃ 949 SO₂ CF₃ Cl CH₃ 950 SO₂ OCHF₂ ClCH₃ 951 bond F Cl CH₂CH₃ 952 bond Cl Cl CH₂CH₃ 953 bond Br Cl CH₂CH₃ 954bond NO₂ Cl CH₂CH₃ 955 bond SCH₃ Cl CH₂CH₃ 956 bond SO₂CH₃ Cl CH₂CH₃ 957bond SO₂CH₂CH₃ Cl CH₂CH₃ 958 bond CH₃ Cl CH₂CH₃ 959 bond CF₃ Cl CH₂CH₃960 bond OCHF₂ Cl CH₂CH₃ 961 CH₂ F Cl CH₂CH₃ 962 CH₂ Cl Cl CH₂CH₃ 963CH₂ Br Cl CH₂CH₃ 964 CH₂ NO₂ Cl CH₂CH₃ 965 CH₂ SCH₃ Cl CH₂CH₃ 966 CH₂SO₂CH₃ Cl CH₂CH₃ 967 CH₂ SO₂CH₂CH₃ Cl CH₂CH₃ 968 CH₂ CH₃ Cl CH₂CH₃ 969CH₂ CF₃ Cl CH₂CH₃ 970 CH₂ OCHF₂ Cl CH₂CH₃ 971 O F Cl CH₂CH₃ 972 O Cl ClCH₂CH₃ 973 O Br Cl CH₂CH₃ 974 O NO₂ Cl CH₂CH₃ 975 O SCH₃ Cl CH₂CH₃ 976 OSO₂CH₃ Cl CH₂CH₃ 977 O SO₂CH₂CH₃ Cl CH₂CH₃ 978 O CH₃ Cl CH₂CH₃ 979 O CF₃Cl CH₂CH₃ 980 O OCHF₂ Cl CH₂CH₃ 981 S F Cl CH₂CH₃ 982 S Cl Cl CH₂CH₃ 983S Br Cl CH₂CH₃ 984 S NO₂ Cl CH₂CH₃ 985 S SCH₃ Cl CH₂CH₃ 986 S SO₂CH₃ ClCH₂CH₃ 987 S SO₂CH₂CH₃ Cl CH₂CH₃ 988 S CH₃ Cl CH₂CH₃ 989 S CF₃ Cl CH₂CH₃990 S OCHF₂ Cl CH₂CH₃ 991 SO₂ F Cl CH₂CH₃ 992 SO₂ Cl Cl CH₂CH₃ 993 SO₂Br Cl CH₂CH₃ 994 SO₂ NO₂ Cl CH₂CH₃ 995 SO₂ SCH₃ Cl CH₂CH₃ 996 SO₂ SO₂CH₃Cl CH₂CH₃ 997 SO₂ SO₂CH₂CH₃ Cl CH₂CH₃ 998 SO₂ CH₃ Cl CH₂CH₃ 999 SO₂ CF₃Cl CH₂CH₃ 1000 SO₂ OCHF₂ Cl CH₂CH₃ 1001 bond F OH CH(CH₃)₂ 1002 bond ClOH CH(CH₃)₂ 1003 bond Br OH CH(CH₃)₂ 1004 bond NO₂ OH CH(CH₃)₂ 1005 bondSCH₃ OH CH(CH₃)₂ 1006 bond SO₂CH₃ OH CH(CH₃)₂ 1007 bond SO₂CH₂CH₃ OHCH(CH₃)₂ 1008 bond CH₃ OH CH(CH₃)₂ 1009 bond CF₃ OH CH(CH₃)₂ 1010 bondOCHF₂ OH CH(CH₃)₂ 1011 CH₂ F OH CH(CH₃)₂ 1012 CH₂ Cl OH CH(CH₃)₂ 2025CH₂ Br OH CH(CH₃)₂ 2026 CH₂ NO₂ OH CH(CH₃)₂ 2027 CH₂ SCH₃ OH CH(CH₃)₂2028 CH₂ SO₂CH₃ OH CH(CH₃)₂ 2029 CH₂ SO₂CH₂CH₃ OH CH(CH₃)₂ 2030 CH₂ CH₃OH CH(CH₃)₂ 2031 CH₂ CF₃ OH CH(CH₃)₂ 2032 CH₂ OCHF₂ OH CH(CH₃)₂ 2033 O FOH CH(CH₃)₂ 2034 O Cl OH CH(CH₃)₂ 2035 O Br OH CH(CH₃)₂ 2036 O NO₂ OHCH(CH₃)₂ 2037 O SCH₃ OH CH(CH₃)₂ 2038 O SO₂CH₃ OH CH(CH₃)₂ 2039 OSO₂CH₂CH₃ OH CH(CH₃)₂ 2040 O CH₃ OH CH(CH₃)₂ 2041 O CF₃ OH CH(CH₃)₂ 2042O OCHF₂ OH CH(CH₃)₂ 2043 S F OH CH(CH₃)₂ 2044 S Cl OH CH(CH₃)₂ 2045 S BrOH CH(CH₃)₂ 2046 S NO₂ OH CH(CH₃)₂ 2047 S SCH₃ OH CH(CH₃)₂ 2048 S SO₂CH₃OH CH(CH₃)₂ 2049 S SO₂CH₂CH₃ OH CH(CH₃)₂ 2050 S CH₃ OH CH(CH₃)₂ 2051 SCF₃ OH CH(CH₃)₂ 2052 S OCHF₂ OH CH(CH₃)₂ 2053 SO₂ F OH CH(CH₃)₂ 2054 SO₂Cl OH CH(CH₃)₂ 2055 SO₂ Br OH CH(CH₃)₂ 2056 SO₂ NO₂ OH CH(CH₃)₂ 2057 SO₂SCH₃ OH CH(CH₃)₂ 2058 SO₂ SO₂CH₃ OH CH(CH₃)₂ 2059 SO₂ SO₂CH₂CH₃ OHCH(CH₃)₂ 2060 SO₂ CH₃ OH CH(CH₃)₂ 2061 SO₂ CF₃ OH CH(CH₃)₂ 2062 SO₂OCHF₂ OH CH(CH₃)₂ 2063 bond F OH C(CH₃)₃ 2064 bond Cl OH C(CH₃)₃ 2065bond Br OH C(CH₃)₃ 2066 bond NO₂ OH C(CH₃)₃ 2067 bond SCH₃ OH C(CH₃)₃2068 bond SO₂CH₃ OH C(CH₃)₃ 2069 bond SO₂CH₂CH₃ OH C(CH₃)₃ 2070 bond CH₃OH C(CH₃)₃ 2071 bond CF₃ OH C(CH₃)₃ 2072 bond OCHF₂ OH C(CH₃)₃ 2073 CH₂F OH C(CH₃)₃ 2074 CH₂ Cl OH C(CH₃)₃ 2075 CH₂ Br OH C(CH₃)₃ 2076 CH₂ NO₂OH C(CH₃)₃ 2077 CH₂ SCH₃ OH C(CH₃)₃ 2078 CH₂ SO₂CH₃ OH C(CH₃)₃ 2079 CH₂SO₂CH₂CH₃ OH C(CH₃)₃ 2080 CH₂ CH₃ OH C(CH₃)₃ 2081 CH₂ CF₃ OH C(CH₃)₃2082 CH₂ OCHF₂ OH C(CH₃)₃ 2083 O F OH C(CH₃)₃ 2084 O Cl OH C(CH₃)₃ 2085O Br OH C(CH₃)₃ 2086 O NO₂ OH C(CH₃)₃ 2087 O SCH₃ OH C(CH₃)₃ 2088 OSO₂CH₃ OH C(CH₃)₃ 2089 O SO₂CH₂CH₃ OH C(CH₃)₃ 2090 O CH₃ OH C(CH₃)₃ 2091O CF₃ OH C(CH₃)₃ 2092 O OCHF₂ OH C(CH₃)₃ 2093 S F OH C(CH₃)₃ 2094 S ClOH C(CH₃)₃ 2095 S Br OH C(CH₃)₃ 2096 S NO₂ OH C(CH₃)₃ 2097 S SCH₃ OHC(CH₃)₃ 2098 S SO₂CH₃ OH C(CH₃)₃ 2099 S SO₂CH₂CH₃ OH C(CH₃)₃ 2100 S CH₃OH C(CH₃)₃ 2101 S CF₃ OH C(CH₃)₃ 2102 S OCHF₂ OH C(CH₃)₃ 2103 SO₂ F OHC(CH₃)₃ 2104 SO₂ Cl OH C(CH₃)₃ 2105 SO₂ Br OH C(CH₃)₃ 2106 SO₂ NO₂ OHC(CH₃)₃ 2107 SO₂ SCH₃ OH C(CH₃)₃ 2108 SO₂ SO₂CH₃ OH C(CH₃)₃ 2109 SO₂SO₂CH₂CH₃ OH C(CH₃)₃ 2110 SO₂ CH₃ OH C(CH₃)₃ 2111 SO₂ CF₃ OH C(CH₃)₃2112 SO₂ OCHF₂ OH C(CH₃)₃ 2113 bond F OCOC₆H₅ CH(CH₃)₂ 2114 bond ClOCOC₆H₅ CH(CH₃)₂ 2115 bond Br OCOC₆H₅ CH(CH₃)₂ 2116 bond NO₂ OCOC₆H₅CH(CH₃)₂ 2117 bond SCH₃ OCOC₆H₅ CH(CH₃)₂ 2118 bond SO₂CH₃ OCOC₆H₅CH(CH₃)₂ 2119 bond SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 2120 bond CH₃ OCOC₆H₅CH(CH₃)₂ 2121 bond CF₃ OCOC₆H₅ CH(CH₃)₂ 2122 bond OCHF₂ OCOC₆H₅ CH(CH₃)₂2123 CH₂ F OCOC₆H₅ CH(CH₃)₂ 2124 CH₂ Cl OCOC₆H₅ CH(CH₃)₂ 2125 CH₂ BrOCOC₆H₅ CH(CH₃)₂ 2126 CH₂ NO₂ OCOC₆H₅ CH(CH₃)₂ 2127 CH₂ SCH₃ OCOC₆H₅CH(CH₃)₂ 2128 CH₂ SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 2129 CH₂ SO₂CH₂CH₃ OCOC₆H₅CH(CH₃)₂ 2130 CH₂ CH₃ OCOC₆H₅ CH(CH₃)₂ 2131 CH₂ CF₃ OCOC₆H₅ CH(CH₃)₂2132 CH₂ OCHF₂ OCOC₆H₅ CH(CH₃)₂ 2133 O F OCOC₆H₅ CH(CH₃)₂ 2134 O ClOCOC₆H₅ CH(CH₃)₂ 2135 O Br OCOC₆H₅ CH(CH₃)₂ 2136 O NO₂ OCOC₆H₅ CH(CH₃)₂2137 O SCH₃ OCOC₆H₅ CH(CH₃)₂ 2138 O SO₂CH₃ OCOC₆H₅ CH(CH₃)₂ 2139 OSO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 2140 O CH₃ OCOC₆H₅ CH(CH₃)₂ 2141 O CF₃OCOC₆H₅ CH(CH₃)₂ 2142 O OCHF₂ OCOC₆H₅ CH(CH₃)₂ 2143 S F OCOC₆H₅ CH(CH₃)₂2144 S Cl OCOC₆H₅ CH(CH₃)₂ 2145 S Br OCOC₆H₅ CH(CH₃)₂ 2146 S NO₂ OCOC₆H₅CH(CH₃)₂ 2147 S SCH₃ OCOC₆H₅ CH(CH₃)₂ 2148 S SO₂CH₃ OCOC₆H₅ CH(CH₃)₂2149 S SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 2150 S CH₃ OCOC₆H₅ CH(CH₃)₂ 2151 S CF₃OCOC₆H₅ CH(CH₃)₂ 2152 S OCHF₂ OCOC₆H₅ CH(CH₃)₂ 2153 SO₂ F OCOC₆H₅CH(CH₃)₂ 2154 SO₂ Cl OCOC₆H₅ CH(CH₃)₂ 2155 SO₂ Br OCOC₆H₅ CH(CH₃)₂ 2156SO₂ NO₂ OCOC₆H₅ CH(CH₃)₂ 2157 SO₂ SCH₃ OCOC₆H₅ CH(CH₃)₂ 2158 SO₂ SO₂CH₃OCOC₆H₅ CH(CH₃)₂ 2159 SO₂ SO₂CH₂CH₃ OCOC₆H₅ CH(CH₃)₂ 2160 SO₂ CH₃OCOC₆H₅ CH(CH₃)₂ 2161 SO₂ CF₃ OCOC₆H₅ CH(CH₃)₂ 2162 SO₂ OCHF₂ OCOC₆H₅CH(CH₃)₂ 2163 bond F OCOC₆H₅ C(CH₃)₃ 2164 bond Cl OCOC₆H₅ C(CH₃)₃ 2165bond Br OCOC₆H₅ C(CH₃)₃ 2166 bond NO₂ OCOC₆H₅ C(CH₃)₃ 2167 bond SCH₃OCOC₆H₅ C(CH₃)₃ 2168 bond SO₂CH₃ OCOC₆H₅ C(CH₃)₃ 2169 bond SO₂CH₂CH₃OCOC₆H₅ C(CH₃)₃ 2170 bond CH₃ OCOC₆H₅ C(CH₃)₃ 2171 bond CF₃ OCOC₆H₅C(CH₃)₃ 2172 bond OCHF₂ OCOC₆H₅ C(CH₃)₃ 2173 CH₂ F OCOC₆H₅ C(CH₃)₃ 2174CH₂ Cl OCOC₆H₅ C(CH₃)₃ 2175 CH₂ Br OCOC₆H₅ C(CH₃)₃ 2176 CH₂ NO₂ OCOC₆H₅C(CH₃)₃ 2177 CH₂ SCH₃ OCOC₆H₅ C(CH₃)₃ 2178 CH₂ SO₂CH₃ OCOC₆H₅ C(CH₃)₃2179 CH₂ SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 2180 CH₂ CH₃ OCOC₆H₅ C(CH₃)₃ 2181 CH₂CF₃ OCOC₆H₅ C(CH₃)₃ 2182 CH₂ OCHF₂ OCOC₆H₅ C(CH₃)₃ 2183 O F OCOC₆H₅C(CH₃)₃ 2184 O Cl OCOC₆H₅ C(CH₃)₃ 2185 O Br OCOC₆H₅ C(CH₃)₃ 2186 O NO₂OCOC₆H₅ C(CH₃)₃ 2187 O SCH₃ OCOC₆H₅ C(CH₃)₃ 2188 O SO₂CH₃ OCOC₆H₅C(CH₃)₃ 2189 O SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 2190 O CH₃ OCOC₆H₅ C(CH₃)₃ 2191O CF₃ OCOC₆H₅ C(CH₃)₃ 2192 O OCHF₂ OCOC₆H₅ C(CH₃)₃ 2193 S F OCOC₆H₅C(CH₃)₃ 2194 S Cl OCOC₆H₅ C(CH₃)₃ 2195 S Br OCOC₆H₅ C(CH₃)₃ 2196 S NO₂OCOC₆H₅ C(CH₃)₃ 2197 S SCH₃ OCOC₆H₅ C(CH₃)₃ 2198 S SO₂CH₃ OCOC₆H₅C(CH₃)₃ 2199 S SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 2200 S CH₃ OCOC₆H₅ C(CH₃)₃ 2201S CF₃ OCOC₆H₅ C(CH₃)₃ 2202 S OCHF₂ OCOC₆H₅ C(CH₃)₃ 2203 SO₂ F OCOC₆H₅C(CH₃)₃ 2204 SO₂ Cl OCOC₆H₅ C(CH₃)₃ 2205 SO₂ Br OCOC₆H₅ C(CH₃)₃ 2206 SO₂NO₂ OCOC₆H₅ C(CH₃)₃ 2207 SO₂ SCH₃ OCOC₆H₅ C(CH₃)₃ 2208 SO₂ SO₂CH₃OCOC₆H₅ C(CH₃)₃ 2209 SO₂ SO₂CH₂CH₃ OCOC₆H₅ C(CH₃)₃ 2210 SO₂ CH₃ OCOC₆H₅C(CH₃)₃ 2211 SO₂ CF₃ OCOC₆H₅ C(CH₃)₃ 2212 SO₂ OCHF₂ OCOC₆H₅ C(CH₃)₃ 2213bond F OCOC(CH₃)₃ CH(CH₃)₂ 2214 bond Cl OCOC(CH₃)₃ CH(CH₃)₂ 2215 bond BrOCOC(CH₃)₃ CH(CH₃)₂ 2216 bond NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 2217 bond SCH₃OCOC(CH₃)₃ CH(CH₃)₂ 2218 bond SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2219 bondSO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2220 bond CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2221bond CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 2222 bond OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 2223CH₂ F OCOC(CH₃)₃ CH(CH₃)₂ 2224 CH₂ Cl OCOC(CH₃)₃ CH(CH₃)₂ 2225 CH₂ BrOCOC(CH₃)₃ CH(CH₃)₂ 2226 CH₂ NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 2227 CH₂ SCH₃OCOC(CH₃)₃ CH(CH₃)₂ 2228 CH₂ SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2229 CH₂SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2230 CH₂ CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2231 CH₂CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 2232 CH₂ OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 2233 O FOCOC(CH₃)₃ CH(CH₃)₂ 2234 O Cl OCOC(CH₃)₃ CH(CH₃)₂ 2235 O Br OCOC(CH₃)₃CH(CH₃)₂ 2236 O NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 2237 O SCH₃ OCOC(CH₃)₃ CH(CH₃)₂2238 O SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2239 O SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂2240 O CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2241 O CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 2242 OOCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 2243 S F OCOC(CH₃)₃ CH(CH₃)₂ 2244 S ClOCOC(CH₃)₃ CH(CH₃)₂ 2245 S Br OCOC(CH₃)₃ CH(CH₃)₂ 2246 S NO₂ OCOC(CH₃)₃CH(CH₃)₂ 2247 S SCH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2248 S SO₂CH₃ OCOC(CH₃)₃CH(CH₃)₂ 2249 S SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2250 S CH₃ OCOC(CH₃)₃CH(CH₃)₂ 2251 S CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 2252 S OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂2253 SO₂ F OCOC(CH₃)₃ CH(CH₃)₂ 2254 SO₂ Cl OCOC(CH₃)₃ CH(CH₃)₂ 2255 SO₂Br OCOC(CH₃)₃ CH(CH₃)₂ 2256 SO₂ NO₂ OCOC(CH₃)₃ CH(CH₃)₂ 2257 SO₂ SCH₃OCOC(CH₃)₃ CH(CH₃)₂ 2258 SO₂ SO₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2259 SO₂SO₂CH₂CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2260 SO₂ CH₃ OCOC(CH₃)₃ CH(CH₃)₂ 2261 SO₂CF₃ OCOC(CH₃)₃ CH(CH₃)₂ 2262 SO₂ OCHF₂ OCOC(CH₃)₃ CH(CH₃)₂ 2263 bond FOCOC(CH₃)₃ C(CH₃)₃ 2264 bond Cl OCOC(CH₃)₃ C(CH₃)₃ 2265 bond BrOCOC(CH₃)₃ C(CH₃)₃ 2266 bond NO₂ OCOC(CH₃)₃ C(CH₃)₃ 2267 bond SCH₃OCOC(CH₃)₃ C(CH₃)₃ 2268 bond SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2269 bondSO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2270 bond CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2271 bondCF₃ OCOC(CH₃)₃ C(CH₃)₃ 2272 bond OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 2273 CH₂ FOCOC(CH₃)₃ C(CH₃)₃ 2274 CH₂ Cl OCOC(CH₃)₃ C(CH₃)₃ 2275 CH₂ Br OCOC(CH₃)₃C(CH₃)₃ 2276 CH₂ NO₂ OCOC(CH₃)₃ C(CH₃)₃ 2277 CH₂ SCH₃ OCOC(CH₃)₃ C(CH₃)₃2278 CH₂ SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2279 CH₂ SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃2280 CH₂ CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2281 CH₂ CF₃ OCOC(CH₃)₃ C(CH₃)₃ 2282 CH₂OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 2283 O F OCOC(CH₃)₃ C(CH₃)₃ 2284 O ClOCOC(CH₃)₃ C(CH₃)₃ 2285 O Br OCOC(CH₃)₃ C(CH₃)₃ 2286 O NO₂ OCOC(CH₃)₃C(CH₃)₃ 2287 O SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 2288 O SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃2289 O SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2290 O CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2291 OCF₃ OCOC(CH₃)₃ C(CH₃)₃ 2292 O OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 2293 S FOCOC(CH₃)₃ C(CH₃)₃ 2294 S Cl OCOC(CH₃)₃ C(CH₃)₃ 2295 S Br OCOC(CH₃)₃C(CH₃)₃ 2296 S NO₂ OCOC(CH₃)₃ C(CH₃)₃ 2297 S SCH₃ OCOC(CH₃)₃ C(CH₃)₃2298 S SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2299 S SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃2300 S CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2301 S CF₃ OCOC(CH₃)₃ C(CH₃)₃ 2302 S OCHF₂OCOC(CH₃)₃ C(CH₃)₃ 2303 SO₂ F OCOC(CH₃)₃ C(CH₃)₃ 2304 SO₂ Cl OCOC(CH₃)₃C(CH₃)₃ 2305 SO₂ Br OCOC(CH₃)₃ C(CH₃)₃ 2306 SO₂ NO₂ OCOC(CH₃)₃ C(CH₃)₃2307 SO₂ SCH₃ OCOC(CH₃)₃ C(CH₃)₃ 2308 SO₂ SO₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2309SO₂ SO₂CH₂CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2310 SO₂ CH₃ OCOC(CH₃)₃ C(CH₃)₃ 2311SO₂ CF₃ OCOC(CH₃)₃ C(CH₃)₃ 2312 SO₂ OCHF₂ OCOC(CH₃)₃ C(CH₃)₃ 2313 bond FOCOSCH₃ CH(CH₃)₂ 2314 bond Cl OCOSCH₃ CH(CH₃)₂ 2315 bond Br OCOSCH₃CH(CH₃)₂ 2316 bond NO₂ OCOSCH₃ CH(CH₃)₂ 2317 bond SCH₃ OCOSCH₃ CH(CH₃)₂2318 bond SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 2319 bond SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂2320 bond CH₃ OCOSCH₃ CH(CH₃)₂ 2321 bond CF₃ OCOSCH₃ CH(CH₃)₂ 2322 bondOCHF₂ OCOSCH₃ CH(CH₃)₂ 2323 CH₂ F OCOSCH₃ CH(CH₃)₂ 2324 CH₂ Cl OCOSCH₃CH(CH₃)₂ 2325 CH₂ Br OCOSCH₃ CH(CH₃)₂ 2326 CH₂ NO₂ OCOSCH₃ CH(CH₃)₂ 2327CH₂ SCH₃ OCOSCH₃ CH(CH₃)₂ 2328 CH₂ SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 2329 CH₂SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 2330 CH₂ CH₃ OCOSCH₃ CH(CH₃)₂ 2331 CH₂ CF₃OCOSCH₃ CH(CH₃)₂ 2332 CH₂ OCHF₂ OCOSCH₃ CH(CH₃)₂ 2333 O F OCOSCH₃CH(CH₃)₂ 2334 O Cl OCOSCH₃ CH(CH₃)₂ 2335 O Br OCOSCH₃ CH(CH₃)₂ 2336 ONO₂ OCOSCH₃ CH(CH₃)₂ 2337 O SCH₃ OCOSCH₃ CH(CH₃)₂ 2338 O SO₂CH₃ OCOSCH₃CH(CH₃)₂ 2339 O SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 2340 O CH₃ OCOSCH₃ CH(CH₃)₂2341 O CF₃ OCOSCH₃ CH(CH₃)₂ 2342 O OCHF₂ OCOSCH₃ CH(CH₃)₂ 2343 S FOCOSCH₃ CH(CH₃)₂ 2344 S Cl OCOSCH₃ CH(CH₃)₂ 2345 S Br OCOSCH₃ CH(CH₃)₂2346 S NO₂ OCOSCH₃ CH(CH₃)₂ 2347 S SCH₃ OCOSCH₃ CH(CH₃)₂ 2348 S SO₂CH₃OCOSCH₃ CH(CH₃)₂ 2349 S SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂ 2350 S CH₃ OCOSCH₃CH(CH₃)₂ 2351 S CF₃ OCOSCH₃ CH(CH₃)₂ 2352 S OCHF₂ OCOSCH₃ CH(CH₃)₂ 2353SO₂ F OCOSCH₃ CH(CH₃)₂ 2354 SO₂ Cl OCOSCH₃ CH(CH₃)₂ 2355 SO₂ Br OCOSCH₃CH(CH₃)₂ 2356 SO₂ NO₂ OCOSCH₃ CH(CH₃)₂ 2357 SO₂ SCH₃ OCOSCH₃ CH(CH₃)₂2358 SO₂ SO₂CH₃ OCOSCH₃ CH(CH₃)₂ 2359 SO₂ SO₂CH₂CH₃ OCOSCH₃ CH(CH₃)₂2360 SO₂ CH₃ OCOSCH₃ CH(CH₃)₂ 2361 SO₂ CF₃ OCOSCH₃ CH(CH₃)₂ 2362 SO₂OCHF₂ OCOSCH₃ CH(CH₃)₂ 2363 bond F OCOSCH₃ C(CH₃)₃ 2364 bond Cl OCOSCH₃C(CH₃)₃ 2365 bond Br OCOSCH₃ C(CH₃)₃ 2366 bond NO₂ OCOSCH₃ C(CH₃)₃ 2367bond SCH₃ OCOSCH₃ C(CH₃)₃ 2368 bond SO₂CH₃ OCOSCH₃ C(CH₃)₃ 2369 bondSO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 2370 bond CH₃ OCOSCH₃ C(CH₃)₃ 2371 bond CF₃OCOSCH₃ C(CH₃)₃ 2372 bond OCHF₂ OCOSCH₃ C(CH₃)₃ 2373 CH₂ F OCOSCH₃C(CH₃)₃ 2374 CH₂ Cl OCOSCH₃ C(CH₃)₃ 2375 CH₂ Br OCOSCH₃ C(CH₃)₃ 2376 CH₂NO₂ OCOSCH₃ C(CH₃)₃ 2377 CH₂ SCH₃ OCOSCH₃ C(CH₃)₃ 2378 CH₂ SO₂CH₃OCOSCH₃ C(CH₃)₃ 2379 CH₂ SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 2380 CH₂ CH₃ OCOSCH₃C(CH₃)₃ 2381 CH₂ CF₃ OCOSCH₃ C(CH₃)₃ 2382 CH₂ OCHF₂ OCOSCH₃ C(CH₃)₃ 2383O F OCOSCH₃ C(CH₃)₃ 2384 O Cl OCOSCH₃ C(CH₃)₃ 2385 O Br OCOSCH₃ C(CH₃)₃2386 O NO₂ OCOSCH₃ C(CH₃)₃ 2387 O SCH₃ OCOSCH₃ C(CH₃)₃ 2388 O SO₂CH₃OCOSCH₃ C(CH₃)₃ 2389 O SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 2390 O CH₃ OCOSCH₃C(CH₃)₃ 2391 O CF₃ OCOSCH₃ C(CH₃)₃ 2392 O OCHF₂ OCOSCH₃ C(CH₃)₃ 2393 S FOCOSCH₃ C(CH₃)₃ 2394 S Cl OCOSCH₃ C(CH₃)₃ 2395 S Br OCOSCH₃ C(CH₃)₃ 2396S NO₂ OCOSCH₃ C(CH₃)₃ 2397 S SCH₃ OCOSCH₃ C(CH₃)₃ 2398 S SO₂CH₃ OCOSCH₃C(CH₃)₃ 2399 S SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 2400 S CH₃ OCOSCH₃ C(CH₃)₃ 2401S CF₃ OCOSCH₃ C(CH₃)₃ 2402 S OCHF₂ OCOSCH₃ C(CH₃)₃ 2403 SO₂ F OCOSCH₃C(CH₃)₃ 2404 SO₂ Cl OCOSCH₃ C(CH₃)₃ 2405 SO₂ Br OCOSCH₃ C(CH₃)₃ 2406 SO₂NO₂ OCOSCH₃ C(CH₃)₃ 2407 SO₂ SCH₃ OCOSCH₃ C(CH₃)₃ 2408 SO₂ SO₂CH₃OCOSCH₃ C(CH₃)₃ 2409 SO₂ SO₂CH₂CH₃ OCOSCH₃ C(CH₃)₃ 2410 SO₂ CH₃ OCOSCH₃C(CH₃)₃ 2411 SO₂ CF₃ OCOSCH₃ C(CH₃)₃ 2412 SO₂ OCHF₂ OCOSCH₃ C(CH₃)₃ 2413bond F OCH₃ CH(CH₃)₂ 2414 bond Cl OCH₃ CH(CH₃)₂ 2415 bond Br OCH₃CH(CH₃)₂ 2416 bond NO₂ OCH₃ CH(CH₃)₂ 2417 bond SCH₃ OCH₃ CH(CH₃)₂ 2418bond SO₂CH₃ OCH₃ CH(CH₃)₂ 2419 bond SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 2420 bondCH₃ OCH₃ CH(CH₃)₂ 2421 bond CF₃ OCH₃ CH(CH₃)₂ 2422 bond OCHF₂ OCH₃CH(CH₃)₂ 2423 CH₂ F OCH₃ CH(CH₃)₂ 2424 CH₂ Cl OCH₃ CH(CH₃)₂ 2425 CH₂ BrOCH₃ CH(CH₃)₂ 2426 CH₂ NO₂ OCH₃ CH(CH₃)₂ 2427 CH₂ SCH₃ OCH₃ CH(CH₃)₂2428 CH₂ SO₂CH₃ OCH₃ CH(CH₃)₂ 2429 CH₂ SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 2430 CH₂CH₃ OCH₃ CH(CH₃)₂ 2431 CH₂ CF₃ OCH₃ CH(CH₃)₂ 2432 CH₂ OCHF₂ OCH₃CH(CH₃)₂ 2433 O F OCH₃ CH(CH₃)₂ 2434 O Cl OCH₃ CH(CH₃)₂ 2435 O Br OCH₃CH(CH₃)₂ 2436 O NO₂ OCH₃ CH(CH₃)₂ 2437 O SCH₃ OCH₃ CH(CH₃)₂ 2438 OSO₂CH₃ OCH₃ CH(CH₃)₂ 2439 O SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 2440 O CH₃ OCH₃CH(CH₃)₂ 2441 O CF₃ OCH₃ CH(CH₃)₂ 2442 O OCHF₂ OCH₃ CH(CH₃)₂ 2443 S FOCH₃ CH(CH₃)₂ 2444 S Cl OCH₃ CH(CH₃)₂ 2445 S Br OCH₃ CH(CH₃)₂ 2446 S NO₂OCH₃ CH(CH₃)₂ 2447 S SCH₃ OCH₃ CH(CH₃)₂ 2448 S SO₂CH₃ OCH₃ CH(CH₃)₂ 2449S SO₂CH₂CH₃ OCH₃ CH(CH₃)₂ 2450 S CH₃ OCH₃ CH(CH₃)₂ 2451 S CF₃ OCH₃CH(CH₃)₂ 2452 S OCHF₂ OCH₃ CH(CH₃)₂ 2453 SO₂ F OCH₃ CH(CH₃)₂ 2454 SO₂ ClOCH₃ CH(CH₃)₂ 2455 SO₂ Br OCH₃ CH(CH₃)₂ 2456 SO₂ NO₂ OCH₃ CH(CH₃)₂ 2457SO₂ SCH₃ OCH₃ CH(CH₃)₂ 2458 SO₂ SO₂CH₃ OCH₃ CH(CH₃)₂ 2459 SO₂ SO₂CH₂CH₃OCH₃ CH(CH₃)₂ 2460 SO₂ CH₃ OCH₃ CH(CH₃)₂ 2461 SO₂ CF₃ OCH₃ CH(CH₃)₂ 2462SO₂ OCHF₂ OCH₃ CH(CH₃)₂ 2463 bond F OCH₃ C(CH₃)₃ 2464 bond Cl OCH₃C(CH₃)₃ 2465 bond Br OCH₃ C(CH₃)₃ 2466 bond NO₂ OCH₃ C(CH₃)₃ 2467 bondSCH₃ OCH₃ C(CH₃)₃ 2468 bond SO₂CH₃ OCH₃ C(CH₃)₃ 2469 bond SO₂CH₂CH₃ OCH₃C(CH₃)₃ 2470 bond CH₃ OCH₃ C(CH₃)₃ 2471 bond CF₃ OCH₃ C(CH₃)₃ 2472 bondOCHF₂ OCH₃ C(CH₃)₃ 2473 CH₂ F OCH₃ C(CH₃)₃ 2474 CH₂ Cl OCH₃ C(CH₃)₃ 2475CH₂ Br OCH₃ C(CH₃)₃ 2476 CH₂ NO₂ OCH₃ C(CH₃)₃ 2477 CH₂ SCH₃ OCH₃ C(CH₃)₃2478 CH₂ SO₂CH₃ OCH₃ C(CH₃)₃ 2479 CH₂ SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 2480 CH₂CH₃ OCH₃ C(CH₃)₃ 2481 CH₂ CF₃ OCH₃ C(CH₃)₃ 2482 CH₂ OCHF₂ OCH₃ C(CH₃)₃2483 O F OCH₃ C(CH₃)₃ 2484 O Cl OCH₃ C(CH₃)₃ 2485 O Br OCH₃ C(CH₃)₃ 2486O NO₂ OCH₃ C(CH₃)₃ 2487 O SCH₃ OCH₃ C(CH₃)₃ 2488 O SO₂CH₃ OCH₃ C(CH₃)₃2489 O SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 2490 O CH₃ OCH₃ C(CH₃)₃ 2491 O CF₃ OCH₃C(CH₃)₃ 2492 O OCHF₂ OCH₃ C(CH₃)₃ 2493 S F OCH₃ C(CH₃)₃ 2494 S Cl OCH₃C(CH₃)₃ 2495 S Br OCH₃ C(CH₃)₃ 2496 S NO₂ OCH₃ C(CH₃)₃ 2497 S SCH₃ OCH₃C(CH₃)₃ 2498 S SO₂CH₃ OCH₃ C(CH₃)₃ 2499 S SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 2500 SCH₃ OCH₃ C(CH₃)₃ 2501 S CF₃ OCH₃ C(CH₃)₃ 2502 S OCHF₂ OCH₃ C(CH₃)₃ 2503SO₂ F OCH₃ C(CH₃)₃ 2504 SO₂ Cl OCH₃ C(CH₃)₃ 2505 SO₂ Br OCH₃ C(CH₃)₃2506 SO₂ NO₂ OCH₃ C(CH₃)₃ 2507 SO₂ SCH₃ OCH₃ C(CH₃)₃ 2508 SO₂ SO₂CH₃OCH₃ C(CH₃)₃ 2509 SO₂ SO₂CH₂CH₃ OCH₃ C(CH₃)₃ 2510 SO₂ CH₃ OCH₃ C(CH₃)₃2511 SO₂ CF₃ OCH₃ C(CH₃)₃ 2512 SO₂ OCHF₂ OCH₃ C(CH₃)₃ 2513 bond FOCH(CH₃)₂ CH(CH₃)₂ 2514 bond Cl OCH(CH₃)₂ CH(CH₃)₂ 2515 bond BrOCH(CH₃)₂ CH(CH₃)₂ 2516 bond NO₂ OCH(CH₃)₂ CH(CH₃)₂ 2517 bond SCH₃OCH(CH₃)₂ CH(CH₃)₂ 2518 bond SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2519 bondSO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2520 bond CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2521 bondCF₃ OCH(CH₃)₂ CH(CH₃)₂ 2522 bond OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 2523 CH₂ FOCH(CH₃)₂ CH(CH₃)₂ 2524 CH₂ Cl OCH(CH₃)₂ CH(CH₃)₂ 2525 CH₂ Br OCH(CH₃)₂CH(CH₃)₂ 2526 CH₂ NO₂ OCH(CH₃)₂ CH(CH₃)₂ 2527 CH₂ SCH₃ OCH(CH₃)₂CH(CH₃)₂ 2528 CH₂ SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2529 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂CH(CH₃)₂ 2530 CH₂ CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2531 CH₂ CF₃ OCH(CH₃)₂ CH(CH₃)₂2532 CH₂ OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 2533 O F OCH(CH₃)₂ CH(CH₃)₂ 2534 O ClOCH(CH₃)₂ CH(CH₃)₂ 2535 O Br OCH(CH₃)₂ CH(CH₃)₂ 2536 O NO₂ OCH(CH₃)₂CH(CH₃)₂ 2537 O SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 2538 O SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂2539 O SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2540 O CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2541 OCF₃ OCH(CH₃)₂ CH(CH₃)₂ 2542 O OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 2543 S FOCH(CH₃)₂ CH(CH₃)₂ 2544 S Cl OCH(CH₃)₂ CH(CH₃)₂ 2545 S Br OCH(CH₃)₂CH(CH₃)₂ 2546 S NO₂ OCH(CH₃)₂ CH(CH₃)₂ 2547 S SCH₃ OCH(CH₃)₂ CH(CH₃)₂2548 S SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2549 S SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂2550 S CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2551 S CF₃ OCH(CH₃)₂ CH(CH₃)₂ 2552 S OCHF₂OCH(CH₃)₂ CH(CH₃)₂ 2553 SO₂ F OCH(CH₃)₂ CH(CH₃)₂ 2554 SO₂ Cl OCH(CH₃)₂CH(CH₃)₂ 2555 SO₂ Br OCH(CH₃)₂ CH(CH₃)₂ 2556 SO₂ NO₂ OCH(CH₃)₂ CH(CH₃)₂2557 SO₂ SCH₃ OCH(CH₃)₂ CH(CH₃)₂ 2558 SO₂ SO₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2559SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2560 SO₂ CH₃ OCH(CH₃)₂ CH(CH₃)₂ 2561SO₂ CF₃ OCH(CH₃)₂ CH(CH₃)₂ 2562 SO₂ OCHF₂ OCH(CH₃)₂ CH(CH₃)₂ 2563 bond FOCH(CH₃)₂ C(CH₃)₃ 2564 bond Cl OCH(CH₃)₂ C(CH₃)₃ 2565 bond Br OCH(CH₃)₂C(CH₃)₃ 2566 bond NO₂ OCH(CH₃)₂ C(CH₃)₃ 2567 bond SCH₃ OCH(CH₃)₂ C(CH₃)₃2568 bond SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 2569 bond SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃2570 bond CH₃ OCH(CH₃)₂ C(CH₃)₃ 2571 bond CF₃ OCH(CH₃)₂ C(CH₃)₃ 2572bond OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 2573 CH₂ F OCH(CH₃)₂ C(CH₃)₃ 2574 CH₂ ClOCH(CH₃)₂ C(CH₃)₃ 2575 CH₂ Br OCH(CH₃)₂ C(CH₃)₃ 2576 CH₂ NO₂ OCH(CH₃)₂C(CH₃)₃ 2577 CH₂ SCH₃ OCH(CH₃)₂ C(CH₃)₃ 2578 CH₂ SO₂CH₃ OCH(CH₃)₂C(CH₃)₃ 2579 CH₂ SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 2580 CH₂ CH₃ OCH(CH₃)₂C(CH₃)₃ 2581 CH₂ CF₃ OCH(CH₃)₂ C(CH₃)₃ 2582 CH₂ OCHF₂ OCH(CH₃)₂ C(CH₃)₃2583 O F OCH(CH₃)₂ C(CH₃)₃ 2584 O Cl OCH(CH₃)₂ C(CH₃)₃ 2585 O BrOCH(CH₃)₂ C(CH₃)₃ 2586 O NO₂ OCH(CH₃)₂ C(CH₃)₃ 2587 O SCH₃ OCH(CH₃)₂C(CH₃)₃ 2588 O SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 2589 O SO₂CH₂CH₃ OCH(CH₃)₂C(CH₃)₃ 2590 O CH₃ OCH(CH₃)₂ C(CH₃)₃ 2591 O CF₃ OCH(CH₃)₂ C(CH₃)₃ 2592 OOCHF₂ OCH(CH₃)₂ C(CH₃)₃ 2593 S F OCH(CH₃)₂ C(CH₃)₃ 2594 S Cl OCH(CH₃)₂C(CH₃)₃ 2595 S Br OCH(CH₃)₂ C(CH₃)₃ 2596 S NO₂ OCH(CH₃)₂ C(CH₃)₃ 2597 SSCH₃ OCH(CH₃)₂ C(CH₃)₃ 2598 S SO₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 2599 S SO₂CH₂CH₃OCH(CH₃)₂ C(CH₃)₃ 2600 S CH₃ OCH(CH₃)₂ C(CH₃)₃ 2601 S CF₃ OCH(CH₃)₂C(CH₃)₃ 2602 S OCHF₂ OCH(CH₃)₂ C(CH₃)₃ 2603 SO₂ F OCH(CH₃)₂ C(CH₃)₃ 2604SO₂ Cl OCH(CH₃)₂ C(CH₃)₃ 2605 SO₂ Br OCH(CH₃)₂ C(CH₃)₃ 2606 SO₂ NO₂OCH(CH₃)₂ C(CH₃)₃ 2607 SO₂ SCH₃ OCH(CH₃)₂ C(CH₃)₃ 2608 SO₂ SO₂CH₃OCH(CH₃)₂ C(CH₃)₃ 2609 SO₂ SO₂CH₂CH₃ OCH(CH₃)₂ C(CH₃)₃ 2610 SO₂ CH₃OCH(CH₃)₂ C(CH₃)₃ 2611 SO₂ CF₃ OCH(CH₃)₂ C(CH₃)₃ 2612 SO₂ OCHF₂OCH(CH₃)₂ C(CH₃)₃ 2613 bond F OCH₂C₆H₅ CH(CH₃)₂ 2614 bond Cl OCH₂C₆H₅CH(CH₃)₂ 2615 bond Br OCH₂C₆H₅ CH(CH₃)₂ 2616 bond NO₂ OCH₂C₆H₅ CH(CH₃)₂2617 bond SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 2618 bond SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2619bond SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2620 bond CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2621bond CF₃ OCH₂C₆H₅ CH(CH₃)₂ 2622 bond OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 2623 CH₂ FOCH₂C₆H₅ CH(CH₃)₂ 2624 CH₂ Cl OCH₂C₆H₅ CH(CH₃)₂ 2625 CH₂ Br OCH₂C₆H₅CH(CH₃)₂ 2626 CH₂ NO₂ OCH₂C₆H₅ CH(CH₃)₂ 2627 CH₂ SCH₃ OCH₂C₆H₅ CH(CH₃)₂2628 CH₂ SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2629 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂2630 CH₂ CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2631 CH₂ CF₃ OCH₂C₆H₅ CH(CH₃)₂ 2632 CH₂OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 2633 O F OCH₂C₆H₅ CH(CH₃)₂ 2634 O Cl OCH₂C₆H₅CH(CH₃)₂ 2635 O Br OCH₂C₆H₅ CH(CH₃)₂ 2636 O NO₂ OCH₂C₆H₅ CH(CH₃)₂ 2637 OSCH₃ OCH₂C₆H₅ CH(CH₃)₂ 2638 O SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2639 O SO₂CH₂CH₃OCH₂C₆H₅ CH(CH₃)₂ 2640 O CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2641 O CF₃ OCH₂C₆H₅CH(CH₃)₂ 2642 O OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 2643 S F OCH₂C₆H₅ CH(CH₃)₂ 2644S Cl OCH₂C₆H₅ CH(CH₃)₂ 2645 S Br OCH₂C₆H₅ CH(CH₃)₂ 2646 S NO₂ OCH₂C₆H₅CH(CH₃)₂ 2647 S SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 2648 S SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂2649 S SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2650 S CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2651 SCF₃ OCH₂C₆H₅ CH(CH₃)₂ 2652 S OCHF₂ OCH₂C₆H₅ CH(CH₃)₂ 2653 SO₂ F OCH₂C₆H₅CH(CH₃)₂ 2654 SO₂ Cl OCH₂C₆H₅ CH(CH₃)₂ 2655 SO₂ Br OCH₂C₆H₅ CH(CH₃)₂2656 SO₂ NO₂ OCH₂C₆H₅ CH(CH₃)₂ 2657 SO₂ SCH₃ OCH₂C₆H₅ CH(CH₃)₂ 2658 SO₂SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2659 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2660 SO₂CH₃ OCH₂C₆H₅ CH(CH₃)₂ 2661 SO₂ CF₃ OCH₂C₆H₅ CH(CH₃)₂ 2662 SO₂ OCHF₂OCH₂C₆H₅ CH(CH₃)₂ 2663 bond F OCH₂C₆H₅ C(CH₃)₃ 2664 bond Cl OCH₂C₆H₅C(CH₃)₃ 2665 bond Br OCH₂C₆H₅ C(CH₃)₃ 2666 bond NO₂ OCH₂C₆H₅ C(CH₃)₃2667 bond SCH₃ OCH₂C₆H₅ C(CH₃)₃ 2668 bond SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2669bond SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2670 bond CH₃ OCH₂C₆H₅ C(CH₃)₃ 2671 bondCF₃ OCH₂C₆H₅ C(CH₃)₃ 2672 bond OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 2673 CH₂ FOCH₂C₆H₅ C(CH₃)₃ 2674 CH₂ Cl OCH₂C₆H₅ C(CH₃)₃ 2675 CH₂ Br OCH₂C₆H₅C(CH₃)₃ 2676 CH₂ NO₂ OCH₂C₆H₅ C(CH₃)₃ 2677 CH₂ SCH₃ OCH₂C₆H₅ C(CH₃)₃2678 CH₂ SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2679 CH₂ SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃2680 CH₂ CH₃ OCH₂C₆H₅ C(CH₃)₃ 2681 CH₂ CF₃ OCH₂C₆H₅ C(CH₃)₃ 2682 CH₂OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 2683 O F OCH₂C₆H₅ C(CH₃)₃ 2684 O Cl OCH₂C₆H₅C(CH₃)₃ 2685 O Br OCH₂C₆H₅ C(CH₃)₃ 2686 O NO₂ OCH₂C₆H₅ C(CH₃)₃ 2687 OSCH₃ OCH₂C₆H₅ C(CH₃)₃ 2688 O SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2689 O SO₂CH₂CH₃OCH₂C₆H₅ C(CH₃)₃ 2690 O CH₃ OCH₂C₆H₅ C(CH₃)₃ 2691 O CF₃ OCH₂C₆H₅ C(CH₃)₃2692 O OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 2693 S F OCH₂C₆H₅ C(CH₃)₃ 2694 S ClOCH₂C₆H₅ C(CH₃)₃ 2695 S Br OCH₂C₆H₅ C(CH₃)₃ 2696 S NO₂ OCH₂C₆H₅ C(CH₃)₃2697 S SCH₃ OCH₂C₆H₅ C(CH₃)₃ 2698 S SO₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2699 SSO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2700 S CH₃ OCH₂C₆H₅ C(CH₃)₃ 2701 S CF₃OCH₂C₆H₅ C(CH₃)₃ 2702 S OCHF₂ OCH₂C₆H₅ C(CH₃)₃ 2703 SO₂ F OCH₂C₆H₅C(CH₃)₃ 2704 SO₂ Cl OCH₂C₆H₅ C(CH₃)₃ 2705 SO₂ Br OCH₂C₆H₅ C(CH₃)₃ 2706SO₂ NO₂ OCH₂C₆H₅ C(CH₃)₃ 2707 SO₂ SCH₃ OCH₂C₆H₅ C(CH₃)₃ 2708 SO₂ SO₂CH₃OCH₂C₆H₅ C(CH₃)₃ 2709 SO₂ SO₂CH₂CH₃ OCH₂C₆H₅ C(CH₃)₃ 2710 SO₂ CH₃OCH₂C₆H₅ C(CH₃)₃ 2711 SO₂ CF₃ OCH₂C₆H₅ C(CH₃)₃ 2712 SO₂ OCHF₂ OCH₂C₆H₅C(CH₃)₃ 2713 bond F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2714 bond ClOSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2715 bond Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2716bond NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2717 bond SCH₃ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2718 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2719 bond SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2720 bond CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2721bond CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2722 bond OCHF₂ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2723 CH₂ F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2724 CH₂ ClOSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2725 CH₂ Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2726 CH₂NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2727 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂2728 CH₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2729 CH₂ SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2730 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2731CH₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2732 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2733 O F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2734 O Cl OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2735 O Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2736 O NO₂ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2737 O SCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2738 O SO₂CH₃OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2739 O SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂2740 O CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2741 O CF₃ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2742 O OCHF₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2743 S FOSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2744 S Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2745 S BrOSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2746 S NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2747 SSCH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2748 S SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂2749 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2750 S CH₃ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2751 S CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2752 S OCHF₂OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2753 SO₂ F OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2754 SO₂Cl OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2755 SO₂ Br OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2756SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2757 SO₂ SCH₃ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2758 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2759 SO₂ SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2760 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2761SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) CH(CH₃)₂ 2762 SO₂ OCHF₂ OSO₂(4-CH₃—C₆H₄)CH(CH₃)₂ 2763 bond F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2764 bond ClOSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2765 bond Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2766 bondNO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2767 bond SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃2768 bond SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2769 bond SO₂CH₂CH₃OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2770 bond CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2771bond CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2772 bond OCHF₂ OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2773 CH₂ F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2774 CH₂ Cl OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2775 CH₂ Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2776 CH₂ NO₂OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2777 CH₂ SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2778 CH₂SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2779 CH₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2780 CH₂ CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2781 CH₂ CF₃OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2782 CH₂ OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2783 OF OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2784 O Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2785 O BrOSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2786 O NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2787 O SCH₃OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2788 O SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2789 OSO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2790 O CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃2791 O CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2792 O OCHF₂ OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2793 S F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2794 S Cl OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2795 S Br OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2796 S NO₂ OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2797 S SCH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2798 S SO₂CH₃OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2799 S SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2800S CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2801 S CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2802S OCHF₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2803 SO₂ F OSO₂(4-CH₃—C₆H₄) C(CH₃)₃2804 SO₂ Cl OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2805 SO₂ Br OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2806 SO₂ NO₂ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2807 SO₂ SCH₃OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2808 SO₂ SO₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2809SO₂ SO₂CH₂CH₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2810 SO₂ CH₃ OSO₂(4-CH₃—C₆H₄)C(CH₃)₃ 2811 SO₂ CF₃ OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2812 SO₂ OCHF₂OSO₂(4-CH₃—C₆H₄) C(CH₃)₃ 2813 bond F SCH₃ CH(CH₃)₂ 2814 bond Cl SCH₃CH(CH₃)₂ 2815 bond Br SCH₃ CH(CH₃)₂ 2816 bond NO₂ SCH₃ CH(CH₃)₂ 2817bond SCH₃ SCH₃ CH(CH₃)₂ 2818 bond SO₂CH₃ SCH₃ CH(CH₃)₂ 2819 bondSO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 2820 bond CH₃ SCH₃ CH(CH₃)₂ 2821 bond CF₃ SCH₃CH(CH₃)₂ 2822 bond OCHF₂ SCH₃ CH(CH₃)₂ 2823 CH₂ F SCH₃ CH(CH₃)₂ 2824 CH₂Cl SCH₃ CH(CH₃)₂ 2825 CH₂ Br SCH₃ CH(CH₃)₂ 2826 CH₂ NO₂ SCH₃ CH(CH₃)₂2827 CH₂ SCH₃ SCH₃ CH(CH₃)₂ 2828 CH₂ SO₂CH₃ SCH₃ CH(CH₃)₂ 2829 CH₂SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 2830 CH₂ CH₃ SCH₃ CH(CH₃)₂ 2831 CH₂ CF₃ SCH₃CH(CH₃)₂ 2832 CH₂ OCHF₂ SCH₃ CH(CH₃)₂ 2833 O F SCH₃ CH(CH₃)₂ 2834 O ClSCH₃ CH(CH₃)₂ 2835 O Br SCH₃ CH(CH₃)₂ 2836 O NO₂ SCH₃ CH(CH₃)₂ 2837 OSCH₃ SCH₃ CH(CH₃)₂ 2838 O SO₂CH₃ SCH₃ CH(CH₃)₂ 2839 O SO₂CH₂CH₃ SCH₃CH(CH₃)₂ 2840 O CH₃ SCH₃ CH(CH₃)₂ 2841 O CF₃ SCH₃ CH(CH₃)₂ 2842 O OCHF₂SCH₃ CH(CH₃)₂ 2843 S F SCH₃ CH(CH₃)₂ 2844 S Cl SCH₃ CH(CH₃)₂ 2845 S BrSCH₃ CH(CH₃)₂ 2846 S NO₂ SCH₃ CH(CH₃)₂ 2847 S SCH₃ SCH₃ CH(CH₃)₂ 2848 SSO₂CH₃ SCH₃ CH(CH₃)₂ 2849 S SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 2850 S CH₃ SCH₃CH(CH₃)₂ 2851 S CF₃ SCH₃ CH(CH₃)₂ 2852 S OCHF₂ SCH₃ CH(CH₃)₂ 2853 SO₂ FSCH₃ CH(CH₃)₂ 2854 SO₂ Cl SCH₃ CH(CH₃)₂ 2855 SO₂ Br SCH₃ CH(CH₃)₂ 2856SO₂ NO₂ SCH₃ CH(CH₃)₂ 2857 SO₂ SCH₃ SCH₃ CH(CH₃)₂ 2858 SO₂ SO₂CH₃ SCH₃CH(CH₃)₂ 2859 SO₂ SO₂CH₂CH₃ SCH₃ CH(CH₃)₂ 2860 SO₂ CH₃ SCH₃ CH(CH₃)₂2861 SO₂ CF₃ SCH₃ CH(CH₃)₂ 2862 SO₂ OCHF₂ SCH₃ CH(CH₃)₂ 2863 bond F SCH₃C(CH₃)₃ 2864 bond Cl SCH₃ C(CH₃)₃ 2865 bond Br SCH₃ C(CH₃)₃ 2866 bondNO₂ SCH₃ C(CH₃)₃ 2867 bond SCH₃ SCH₃ C(CH₃)₃ 2868 bond SO₂CH₃ SCH₃C(CH₃)₃ 2869 bond SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 2870 bond CH₃ SCH₃ C(CH₃)₃ 2871bond CF₃ SCH₃ C(CH₃)₃ 2872 bond OCHF₂ SCH₃ C(CH₃)₃ 2873 CH₂ F SCH₃C(CH₃)₃ 2874 CH₂ Cl SCH₃ C(CH₃)₃ 2875 CH₂ Br SCH₃ C(CH₃)₃ 2876 CH₂ NO₂SCH₃ C(CH₃)₃ 2877 CH₂ SCH₃ SCH₃ C(CH₃)₃ 2878 CH₂ SO₂CH₃ SCH₃ C(CH₃)₃2879 CH₂ SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 2880 CH₂ CH₃ SCH₃ C(CH₃)₃ 2881 CH₂ CF₃SCH₃ C(CH₃)₃ 2882 CH₂ OCHF₂ SCH₃ C(CH₃)₃ 2883 O F SCH₃ C(CH₃)₃ 2884 O ClSCH₃ C(CH₃)₃ 2885 O Br SCH₃ C(CH₃)₃ 2886 O NO₂ SCH₃ C(CH₃)₃ 2887 O SCH₃SCH₃ C(CH₃)₃ 2888 O SO₂CH₃ SCH₃ C(CH₃)₃ 2889 O SO₂CH₂CH₃ SCH₃ C(CH₃)₃2890 O CH₃ SCH₃ C(CH₃)₃ 2891 O CF₃ SCH₃ C(CH₃)₃ 2892 O OCHF₂ SCH₃C(CH₃)₃ 2893 S F SCH₃ C(CH₃)₃ 2894 S Cl SCH₃ C(CH₃)₃ 2895 S Br SCH₃C(CH₃)₃ 2896 S NO₂ SCH₃ C(CH₃)₃ 2897 S SCH₃ SCH₃ C(CH₃)₃ 2898 S SO₂CH₃SCH₃ C(CH₃)₃ 2899 S SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 2900 S CH₃ SCH₃ C(CH₃)₃ 2901S CF₃ SCH₃ C(CH₃)₃ 2902 S OCHF₂ SCH₃ C(CH₃)₃ 2903 SO₂ F SCH₃ C(CH₃)₃2904 SO₂ Cl SCH₃ C(CH₃)₃ 2905 SO₂ Br SCH₃ C(CH₃)₃ 2906 SO₂ NO₂ SCH₃C(CH₃)₃ 2907 SO₂ SCH₃ SCH₃ C(CH₃)₃ 2908 SO₂ SO₂CH₃ SCH₃ C(CH₃)₃ 2909 SO₂SO₂CH₂CH₃ SCH₃ C(CH₃)₃ 2910 SO₂ CH₃ SCH₃ C(CH₃)₃ 2911 SO₂ CF₃ SCH₃C(CH₃)₃ 2912 SO₂ OCHF₂ SCH₃ C(CH₃)₃ 2913 bond F Cl CH(CH₃)₂ 2914 bond ClCl CH(CH₃)₂ 2915 bond Br Cl CH(CH₃)₂ 2916 bond NO₂ Cl CH(CH₃)₂ 2917 bondSCH₃ Cl CH(CH₃)₂ 2918 bond SO₂CH₃ Cl CH(CH₃)₂ 2919 bond SO₂CH₂CH₃ ClCH(CH₃)₂ 2920 bond CH₃ Cl CH(CH₃)₂ 2921 bond CF₃ Cl CH(CH₃)₂ 2922 bondOCHF₂ Cl CH(CH₃)₂ 2923 CH₂ F Cl CH(CH₃)₂ 2924 CH₂ Cl Cl CH(CH₃)₂ 2925CH₂ Br Cl CH(CH₃)₂ 2926 CH₂ NO₂ Cl CH(CH₃)₂ 2927 CH₂ SCH₃ Cl CH(CH₃)₂2928 CH₂ SO₂CH₃ Cl CH(CH₃)₂ 2929 CH₂ SO₂CH₂CH₃ Cl CH(CH₃)₂ 2930 CH₂ CH₃Cl CH(CH₃)₂ 2931 CH₂ CF₃ Cl CH(CH₃)₂ 2932 CH₂ OCHF₂ Cl CH(CH₃)₂ 2933 O FCl CH(CH₃)₂ 2934 O Cl Cl CH(CH₃)₂ 2935 O Br Cl CH(CH₃)₂ 2936 O NO₂ ClCH(CH₃)₂ 2937 O SCH₃ Cl CH(CH₃)₂ 2938 O SO₂CH₃ Cl CH(CH₃)₂ 2939 OSO₂CH₂CH₃ Cl CH(CH₃)₂ 2940 O CH₃ Cl CH(CH₃)₂ 2941 O CF₃ Cl CH(CH₃)₂ 2942O OCHF₂ Cl CH(CH₃)₂ 2943 S F Cl CH(CH₃)₂ 2944 S Cl Cl CH(CH₃)₂ 2945 S BrCl CH(CH₃)₂ 2946 S NO₂ Cl CH(CH₃)₂ 2947 S SCH₃ Cl CH(CH₃)₂ 2948 S SO₂CH₃Cl CH(CH₃)₂ 2949 S SO₂CH₂CH₃ Cl CH(CH₃)₂ 2950 S CH₃ Cl CH(CH₃)₂ 2951 SCF₃ Cl CH(CH₃)₂ 2952 S OCHF₂ Cl CH(CH₃)₂ 2953 SO₂ F Cl CH(CH₃)₂ 2954 SO₂Cl Cl CH(CH₃)₂ 2955 SO₂ Br Cl CH(CH₃)₂ 2956 SO₂ NO₂ Cl CH(CH₃)₂ 2957 SO₂SCH₃ Cl CH(CH₃)₂ 2958 SO₂ SO₂CH₃ Cl CH(CH₃)₂ 2959 SO₂ SO₂CH₂CH₃ ClCH(CH₃)₂ 2960 SO₂ CH₃ Cl CH(CH₃)₂ 2961 SO₂ CF₃ Cl CH(CH₃)₂ 2962 SO₂OCHF₂ Cl CH(CH₃)₂ 2963 bond F Cl C(CH₃)₃ 2964 bond Cl Cl C(CH₃)₃ 2965bond Br Cl C(CH₃)₃ 2966 bond NO₂ Cl C(CH₃)₃ 2967 bond SCH₃ Cl C(CH₃)₃2968 bond SO₂CH₃ Cl C(CH₃)₃ 2969 bond SO₂CH₂CH₃ Cl C(CH₃)₃ 2970 bond CH₃Cl C(CH₃)₃ 2971 bond CF₃ Cl C(CH₃)₃ 2972 bond OCHF₂ Cl C(CH₃)₃ 2973 CH₂F Cl C(CH₃)₃ 2974 CH₂ Cl Cl C(CH₃)₃ 2975 CH₂ Br Cl C(CH₃)₃ 2976 CH₂ NO₂Cl C(CH₃)₃ 2977 CH₂ SCH₃ Cl C(CH₃)₃ 2978 CH₂ SO₂CH₃ Cl C(CH₃)₃ 2979 CH₂SO₂CH₂CH₃ Cl C(CH₃)₃ 2980 CH₂ CH₃ Cl C(CH₃)₃ 2981 CH₂ CF₃ Cl C(CH₃)₃2982 CH₂ OCHF₂ Cl C(CH₃)₃ 2983 O F Cl C(CH₃)₃ 2984 O Cl Cl C(CH₃)₃ 2985O Br Cl C(CH₃)₃ 2986 O NO₂ Cl C(CH₃)₃ 2987 O SCH₃ Cl C(CH₃)₃ 2988 OSO₂CH₃ Cl C(CH₃)₃ 2989 O SO₂CH₂CH₃ Cl C(CH₃)₃ 2990 O CH₃ Cl C(CH₃)₃ 2991O CF₃ Cl C(CH₃)₃ 2992 O OCHF₂ Cl C(CH₃)₃ 2993 S F Cl C(CH₃)₃ 2994 S ClCl C(CH₃)₃ 2995 S Br Cl C(CH₃)₃ 2996 S NO₂ Cl C(CH₃)₃ 2997 S SCH₃ ClC(CH₃)₃ 2998 S SO₂CH₃ Cl C(CH₃)₃ 2999 S SO₂CH₂CH₃ Cl C(CH₃)₃ 3000 S CH₃Cl C(CH₃)₃ 3001 S CF₃ Cl C(CH₃)₃ 3002 S OCHF₂ Cl C(CH₃)₃ 3003 SO₂ F ClC(CH₃)₃ 3004 SO₂ Cl Cl C(CH₃)₃ 3005 SO₂ Br Cl C(CH₃)₃ 3006 SO₂ NO₂ ClC(CH₃)₃ 3007 SO₂ SCH₃ Cl C(CH₃)₃ 3008 SO₂ SO₂CH₃ Cl C(CH₃)₃ 3009 SO₂SO₂CH₂CH₃ Cl C(CH₃)₃ 3010 SO₂ CH₃ Cl C(CH₃)₃ 3011 SO₂ CF₃ Cl C(CH₃)₃3012 SO₂ OCHF₂ Cl C(CH₃)₃

Very particular preference is also given to the compounds of the formulaIa2 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to thecompounds Ia2.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa3 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to thecompounds Ia3.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa4 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=2), in particular to thecompounds Ia4.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa5 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to thecompounds Ia5.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa6 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=2), in particular to thecompounds Ia6.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa7 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia7.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa8 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH³, l=1), in particular to thecompounds Ia8.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa9 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia9.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa10 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia10.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa11 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia11.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa12 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia12.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa13 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia13.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa14 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to thecompounds Ia14.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa15 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to thecompounds Ia15.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa16 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia16.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa17 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia17.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa18 (≡Ia where R¹, R², R⁵ and R¹²=H, R¹³=CH₃, l=1), in particular tothe compounds Ia18.n, where the variables X, R⁴, R¹⁰ and R¹¹ are asdefined in Table 1.

Very particular preference is also given to the compounds of the formulaIa19 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia19.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa20 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia20.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa21 (≡Ia where R¹, R², R⁵ and R¹²=H, l=0), in particular to thecompounds Ia21.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

Very particular preference is also given to the compounds of the formulaIa22 (≡Ia where R¹, R², R⁵ and R¹²=H, R³=CH₃, l=1), in particular to thecompounds Ia22.n, where the variables X, R⁴, R¹⁰ and R¹¹ are as definedin Table 1.

The tricyclic benzoylpyrazole derivatives of the formula I can beobtained by various routes, for example by one of the followingprocesses:

-   A. Preparation of compounds of the formula I where R¹⁰=halogen by    reacting a tricyclic benzoylpyrazole derivative of the formula Iα    (≡I where R¹⁰=hydroxyl) with a halogenating agent:

-   -   Suitable halogenating agents are, for example, phosgene,        diphosgene, triphosgene, thionyl chloride, oxalyl chloride,        phosphorus oxychloride, phosphorus pentachloride, mesyl        chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl        bromide, phosphorus oxybromide, etc.    -   The starting materials are generally employed in equimolar        amounts. However, it may also be advantageous to employ an        excess of one or the other component.    -   Suitable solvents are, for example, chlorinated hydrocarbons,        such as methylene chloride or 1,2-dichloroethane, aromatic        hydrocarbons, for example toluene, xylene or chlorobenzene,        polar aprotic solvents, such as acetonitrile, dimethylformamide        or dimethyl sulfoxide, or mixtures of these. However, it is also        possible to carry out the reaction in the absence of solvent.    -   The reaction temperature is generally in the range from 0° C. to        the boiling point of the reaction mixture.    -   Work-up can be carried out in a manner known per se to afford        the product.

-   B. Preparation of compounds of the formula I where R¹⁰=OR¹³, by    reacting a tricyclic benzoylpyrazole derivative of the formula Iα    (≡I where R¹⁰=hydroxyl) with an alkylating agent III.

-   -   L¹ is a nucleophilically replaceable leaving group, such as        halogen, for example chlorine or bromine, hetaryl, for example        imidazolyl, carboxylate, for example acetate, or sulfonate, for        example mesylate or triflate, etc.    -   The compounds of the formula III can be employed directly, such        as, for example, in the case of the carbonyl halides, or be        generated in situ, for example activated carboxylic acids (using        carboxylic acid and dicyclohexylcarbodiimide etc.).    -   The starting materials are generally employed in equimolar        amounts. However, it may also be advantageous to employ an        excess of one or the other component.    -   If appropriate, it may also be advantageous to carry out the        reaction in the presence of a base. Here, the reactants and the        base are advantageously employed in equimolar amounts. In        certain cases, an excess of base, for example from 1.5 to 3        molar equivalents, may be advantageous.    -   Suitable bases are tertiary alkylamines, such as triethylamine,        aromatic amines, such as pyridine, alkali metal carbonates, for        example sodium carbonate or potassium carbonate, alkali metal        bicarbonates, for example sodium bicarbonate and potassium        bicarbonate, alkali metal alkoxides, such as sodium methoxide,        sodium ethoxide, potassium tert-butoxide, or alkali metal        hydrides, for example sodium hydride. Preference is given to        using triethylamine or pyridine.    -   Suitable solvents are, for example, chlorinated hydrocarbons,        such as methylene chloride or 1,2-dichloroethane, aromatic        hydrocarbons, for example toluene, xylene or chlorobenzene,        ethers, such as diethyl ether, methyl tert-butyl ether,        tetrahydrofuran or dioxane, polar aprotic solvents, such as        acetonitrile, dimethylformamide or dimethyl sulfoxide, or        esters, such as ethyl acetate, or mixtures of these.    -   The reaction temperature is generally in the range from 0° C. to        the boiling point of the reaction mixture.    -   Work-up can be carried out in a manner known per se to afford        the product.

-   C. Preparation of compounds of the formula I where R¹⁰=OR¹³, SR¹³,    NR¹⁵R¹⁶ or N-bonded heterocyclyl by reacting compounds of the    formula Iβ (≡I where R¹⁰=halogen) with a compound of the formula    IVα, IVβ, IVγ or IVδ, if appropriate in the presence of a base or    with prior formation of salt.

Iβ + HOR¹³ IVα or HSR¹³ IVβ → I (where R¹⁰ = OR¹³, SR¹³, or NR¹⁵R¹⁶ orN-bonded heterocyclyl) HNR¹⁵R¹⁶ IVγ or H(N-bonded IVδ heterocyclyl)

-   -   The starting materials are generally employed in equimolar        amounts. However, it may also be advantageous to employ an        excess of one or the other component.    -   If appropriate, it may also be advantageous to carry out the        reaction in the presence of a base. Here, the reactants and the        base are advantageously employed in equimolar amounts. An excess        of base, for example from 1.5 to 3 molar equivalents, based on        Iβ (where R¹⁰=halogen), may be advantageous in certain cases.    -   Suitable bases are tertiary alkylamines, such as triethylamine,        aromatic amines, such as pyridine, alkali metal carbonates, for        example sodium carbonate or potassium carbonate, alkali metal        bicarbonates, for example sodium bicarbonate and potassium        bicarbonate, alkali metal alkoxides, such as sodium methoxide,        sodium ethoxide, potassium tert-butoxide, or alkali metal        hydrides, for example sodium hydride. Preference is given to        using sodium hydride or potassium tert-butoxide.    -   Suitable solvents are, for example, chlorinated hydrocarbons,        such as methylene chloride or 1,2-dichloroethane, aromatic        hydrocarbons, for example toluene, xylene or chlorobenzene,        ethers, such as diethyl ether, methyl tert-butyl ether,        tetrahydrofuran or dioxane, polar aprotic solvents, such as        acetonitrile, dimethylformamide or dimethyl sulfoxide, or        mixtures of these.    -   The reaction temperature is generally in the range from 0° C. to        the boiling point of the reaction mixture.    -   Work-up can be carried out in a manner known per se to afford        the product.

-   D. Preparation of compounds of the formula I where R¹⁰ SO₂R¹⁴ by    reacting compounds of the formula I where R¹⁰=SR¹⁰ (Iγ) with an    oxidizing agent.

-   -   Suitable oxidizing agents are, for example, m-chloroperbenzoic        acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen        peroxide, if appropriate in the presence of a catalyst, such as        tungstate.    -   The starting materials are generally employed in equimolar        amounts. However, it may also be advantageous to employ an        excess of one or the other component.    -   Suitable solvents are, for example, chlorinated hydrocarbons,        such as methylene chloride or 1,2-dichloroethane, aromatic        hydrocarbons, for example, toluene, xylene or chlorobenzene,        ethers, such as diethyl ether, methyltert-butyl ether,        tetrahydrofuran or dioxane, polar aprotic solvents, such as        acetonitrile or dimethylformamide, or esters, such as ethyl        acetate, or mixtures of these.    -   The reaction temperature is generally in the range from 0° C. to        the boiling point of the reaction mixture.    -   Work-up can be carried out in a manner known per se to afford        the product.

-   E. Preparation of compounds of the formula I where R⁹=IIa (where    R¹⁰≠hydroxyl or mercapto) by reacting a metalated pyrazole    derivative of the formula V with a tricyclic benzoic acid derivative    of the formula VIα:

-   -   Here, M is a metal, in particular an alkali metal, such as        lithium or sodium, an alkaline earth metal, such as, for        example, magnesium, or a transition metal, such as palladium,        nickel, etc. and L² is a nucleophilically replaceable leaving        group, such as halogen, for example chlorine or bromine,        alkylsulfonate, such as mesylate, haloalkylsulfonate, such as        triflate, or cyanide.    -   The reaction is generally carried out at temperatures of from        −100° C. to the reflux temperature of the reaction mixture.        Suitable solvents are inert aprotic solvents, such as ethers,        for example diethyl ether, tetrahydrofuran. The compounds of the        formula VIα are generally employed in excess, but it may also be        advantageous to employ them in equimolar amounts or in        substoichiometric amounts. Work-up is carried out to afford the        product.    -   The metalated pyrazole derivatives of the formula V can be        formed in a manner known per se by reacting pyrazoles which are        halogenated in the 4-position with metals, such as lithium,        sodium, magnesium, etc., or with organometallic compounds, such        as, for example, butyllithium. However, it is also possible to        metalate pyrazoles which are linked in the 4 position to        hydrogen directly, for example with the abovementioned metals or        organometallic compounds. The reactions are generally carried        out in an inert aprotic solvent, preferably in ether, such as        diethyl ether, tetrahydrofuran, etc. The reaction temperature is        in the range from −100° C. to the boiling point of the reaction        mixture. The compounds of the formula V are generally directly        reacted further or generated in situ.

-   F. Preparation of compounds of the formula Iα (═I where    R¹⁰=hydroxyl) by reacting an activated tricyclic benzoic acid of the    formula VIβ or a tricyclic benzoic acid VIγ, preferably activated in    situ, with a pyrazole of the formula VII to give the acylation    product, followed by rearrangement.

L³ is a nucleophilically replaceable leaving group, such as halogen, forexample bromine or chlorine, hetaryl, for example imidazolyl or pyridyl,carboxylate, for example acetate or trifluoroacetate, etc.

The activated tricyclic benzoic acid VIβ can be employed directly, suchas in the case of the tricyclic benzoyl halides, or be generated insitu, for example using dicyclohexylcarbodiimide,triphenylphosphine/azodicarboxylic ester, 2-pyridinedisulfide/triphenylphosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylationreaction in the presence of a base. Here, the reactants and theauxiliary base are advantageously employed in equimolar amounts. Aslight excess of auxiliary base, for example from 1.2 to 1.5 molarequivalents, based on VI, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine, or alkalimetal carbonates. Suitable solvents are, for example, chlorinatedhydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatichydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane,polar aprotic solvents, such as acetonitrile, dimethylformamide ordimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures ofthese.

If tricyclic benzoyl halides are employed as activated carboxylic acidcomponents, it may be advantageous to cool the reaction mixture to 0–10°C. when adding this reaction partner. The mixture is subsequentlystirred at 20–100° C., preferably at 25–50° C., until the reaction hasgone to completion. Work-up is carried out in a customary manner, forexample by pouring the reaction mixture into water and extracting theproduct of value. Solvents which are suitable for this purpose are, inparticular, methylene chloride, diethyl ether and ethyl acetate. Theorganic phase is dried and the solvent removed, and the crude ester canthen be employed for the rearrangement without further purification.

The rearrangement of the esters VIII to give the compounds of theformula Iα is advantageously carried out at from 20 to 100° C. in asolvent and in the presence of a base and, if appropriate, using a cyanocompound as catalyst.

Solvents which may be used are, for example, acetonitrile, methylenechloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene ormixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromaticamines, such as pyridine, or alkali metal carbonates, such as sodiumcarbonate or potassium carbonate, which are preferably employed inequimolar amounts or in an up to four-fold excess, based on the ester.Preference is given to using triethylamine or alkali metal carbonate,preferably in double the equimolar ratio, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanideor potassium cyanide, and organic cyano compounds, such as acetonecyanohydrin or trimethylsilyl cyanide. They are employed in an amount offrom 1 to 50 mol percent, based on the ester. Preference is given tousing acetone cyanohydrin or trimethylsilyl cyanide, for example in anamount of from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up may be carried out in a manner known per se. The reactionmixture is, for example, acidified using dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride or ethyl acetate. Theorganic extract can be extracted with 5–10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified and the resulting precipitateis filtered off with suction and/or extracted with methylene chloride orethyl acetate, the extract being dried and concentrated.

However, it is also possible to generate the ester VIII in situ byreacting a pyrazole of the formula VII, or an alkali metal salt thereof,with a tricyclic benzene derivative of the formula IX in the presence ofcarbon monoxide, a catalyst and a base.

L⁴ is a leaving group, such as halogen, for example chlorine, bromine oriodine, or sulfonate such as mesylate or triflate; preference is givento bromine or triflate.

If appropriate, the ester VIII reacts directly to give the tricyclicbenzoylpyrazole derivative of the formula Iα.

Suitable catalysts are palladium ligand complexes in which the palladiumis present in oxidation state 0, metallic palladium, if appropriateapplied to a support, and preferably palladium(II) salts. The reactionwith palladium(II) salts and metallic palladium is preferably carriedout in the presence of complex ligands.

A suitable palladium(0) ligand complex is, for example,tetrakis(triphenylphosphane)palladium.

Metallic palladium is preferably applied to an inert carrier, such as,for example, activated carbon, silica, alumina, barium sulfate orcalcium carbonate. The reaction is preferably carried out in thepresence of complex ligands, such as, for example, triphenylphosphane.

Suitable palladium(II) salts are, for example, palladium acetate andpalladium chloride. Preference is given to carrying out the reaction inthe presence of complex ligands such as, for example,triphenylphosphane.

Suitable complex ligands for the palladium ligand complexes, or complexligands in whose presence the reaction with metallic palladium orpalladium(II) salts is preferably carried out are tertiary phosphaneswhose structure is represented by the following formulae:

where n is a number from 1 to 4 and the radicals R^(a) to R^(g) areC₁–C₆-alkyl, aryl-C₁–C₂-alkyl or preferably aryl. Aryl is, for example,naphthyl and unsubstituted or substituted phenyl such as, for example,2-tolyl and in particular unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per sestarting from commercially available palladium salts, such as palladiumchloride or palladium acetate, and the corresponding phosphanes, suchas, for example, triphenylphosphane or 1,2-bis(diphenylphosphano)ethane.A large number of complexed palladium salts is also commerciallyavailable. Preferred palladium salts are[(R)-(+)-2,2′-bis(diphenylphosphano)-1,1′-binaphthyl]palladium (II)chloride, bis(triphenylphosphane)palladium(II)acetate and in particularbis(triphenylphosphane)palladium(II) chloride.

The palladium catalyst is generally employed in a concentration of from0.05 to 5 mol %, and preferably of 1–3 mol %.

Suitable bases are tertiary amines, such as, for example,N-methylpiperidine, ethyldiisopropylamine,1,8-bisdimethylaminonaphthalene and in particular triethylamine. Alsosuitable are alkali metal carbonates, such as sodium carbonate orpotassium carbonate. However, mixtures of potassium carbonate andtriethylamine are also suitable.

In general, from 2 to 4 molar equivalents, in particular 2 molarequivalents, of the alkali metal carbonate, and from 1 to 4 molarequivalents, in particular 2 molar equivalents, of the tertiary amineare employed, based on the tricyclic benzene derivative of the formulaIX.

Suitable solvents are nitrites, such as benzonitrile and acetonitrile,amides, such as dimethylformamide, dimethylacetamide,tetra-C₁–C₄-alkylureas or N-methylpyrrolidone, and preferably ethers,such as tetrahydrofuran, methyl tert-butyl ether. Particular preferenceis given to using, as solvents, ethers such as 1,4-dioxane anddimethoxyethane.

The tricyclic benzoyl halides of the formula VIβ where L³=Cl, Br can beprepared in a manner known per se by reacting the tricyclic benzoicacids of the formula VIγ (≡VIb) with halogenating agents such as thionylchloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalylchloride and oxalyl bromide.

In a known manner, the tricyclic benzoic acids of the formula VIγ (≡VIb)can be prepared by acidic or basic hydrolysis from the correspondingesters VIc.

Tricyclic benzoic acid derivatives of the formula VI

where:

-   -   x is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;    -   Y together with the two carbons to which it is attached forms a        saturated, partially saturated or unsaturated 5- or 6-membered        heterocycle which contains one to three identical or different        heteroatoms selected from the following group:    -    oxygen, sulfur or nitrogen;    -   R¹,R²,R⁶,R⁷ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;    -   R³ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy or        C₁–C₆-haloalkoxy;    -   R⁴ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,        C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,        C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,        C₁–C₆-haloalkylsulfonyl, aminosulfonyl,        N-(C₁–C₆-alkyl)-aminosulfonyl, N,N-di(C₁–C₆-alkyl)aminosulfonyl,        N-(C₁–C₆-alkylsulfonyl)amino, N-(C₁–C₆-haloalkylsulfonyl)amino,        N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino or        N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino;    -   R⁵ is hydrogen, C₁–C₆-alkyl or halogen;    -   R⁸ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkylcarbonyl, formyl, C₁–C₆-alkoxycarbonyl,        C₁–C₆-haloalkoxycarbonyl, C₁–C₆-alkylsulfonyl or        C₁–C₆-haloalkylsulfonyl;    -   l is 0, 1 or 2;    -   R¹⁷ is hydroxyl or a radical which can be removed by hydrolysis;        are novel.

Examples of radicals which can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals which can be unsubstituted orsubstituted, halides, heteroaryl radicals which are attached vianitrogen, amino and imino radicals which may be unsubstituted orsubstituted, etc.

Preference is given to tricyclic benzoyl halides VIa (VI whereR¹⁷=halogen)

where the variables X, Y, R¹ to R⁵ and l are as defined under formula VIand

Hal is halogen, in particular chloride or bromide.

Preference is also given to tricyclic benzoic acids of the formula VIb(VI where R¹⁷=hydroxyl; ≡VIγ),

where the variables X, Y, R¹ to R⁵ and l are as defined under formulaVI.

Preference is also given to tricyclic benzoic esters of the formula VIc(VI where R¹⁷=T=C₁–C₆-alkoxy),

where the variables X, Y, R¹ to R⁵ and l are as defined under formula VIand

T is C₁–C₆-alkoxy.

With respect to the variables X, Y, R¹ to R⁵ and l, the particularlypreferred embodiments of the tricyclic benzoic acid derivatives of theformulae VI, VIa, VIb and VIc correspond to those of the tricyclicbenzoylpyrazole derivatives of the formula I.

Particular preference is given to the compounds VI, VIa, VIb and VIcwhere Y together with the two carbons to which it is attached forms thefollowing heterocycles:

Here, extraordinary preference is given to the compounds VI, VIa, VIband VIc where

-   -   R⁴ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy, C₁–C₆-alkylthio or C₁–C₆-alkylsulfonyl; in        particular C₁–C₆-alkylsulfonyl.

The tricyclic benzoic esters VIc can be obtained in different ways.

For example, benzoic esters of the formula X, which are prepared in amanner known per se (cf., for example, Chem. Pharm. Bull. 1985, 33 (8),3336; Helv. Chim. Acta 1987, 70, 1326; J. Chem. Soc. Perkin Trans. 1972,2019; J. Chem. Soc. Perkin Trans. 1991, 2763; Tetrahydron Asymmetry1998, 9, 1137), can be cyclized to cyclic ketones of the formula XI(cf., for example, Chem. Ber. 1923, 56, 1819; J. Chem. Soc. Perkin11991, 2763; J. Med. Chem. 1988, 31, 230; Tetrahedron 1987, 43, 4549;Synlett 1991, 6, 443; Chem. Pharm. Bull. 1985, 33 (8), 3336).Analogously to known processes (cf., for example, J. Heterocyclic Chem.1976, 13, 545; J. Heterocyclic Chem. 1972, 9, 1341; J. Org. Chem. 1978,43, 3015; J. Chem. Soc. Perkin Trans. 11978, 86; J. Org. Chem. 1986, 51,2021), these can be converted into the tricyclic benzoic esters of theformula VIc.

Furthermore, it may be suitable to cyclize the cyclic ketone of theformula XI in a manner known per se (XII), for example using ananhydride or acid anhydride, if appropriate in the presence of catalyticamounts of a Lewis acid, such as boron trifluoride (cf., for example,Can. J. Chem. 1979, 57, 3292; J. Am. Chem. Soc. 1953, 75, 626), followedby reaction with a hydrazine (cf. A. R. Katritzky et al., ComprehensiveHeterocyclic Chemistry, Vol. 5, p. 121, 277–280 (1984), Pergamon Press;J. Org. Chem. 1961, 26, 451; Org. Synth. 1949, 29, 54), where theresulting pyrazole radical can be modified further by customaryprocesses.

Furthermore, the diketone XII can be reacted with hydroxylamine orequivalents thereof (cf. A. R. Katritzky et al., ComprehensiveHeterocyclic Chemistry, Vol. 6, p. 61–64, 118 (1984), Pergamon Press;Chem. Ber. 1967, 100, 3326). This gives the corresponding isoxazolederivatives which can be modified further by customary processes.

It is also possible to react the diketone XII with amidines (cf., forexample, A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry,Vol. 3, p. 112–114 (1924), Pergamon Press; J. Chem. Soc. C 1967, 1922;Org. Synth. 1963, IV, 182). If required, the resulting pyrimidinederivatives can be modified further by customary processes.

In the reactions mentioned above, it is also possible to employ, insteadof the diketone XII, equivalents thereof, such as enol ethers orenamines, which can be prepared analogously to known processes.

It may also be possible to react the cyclic ketone of the formula XIanalogously to known processes with an aldehyde or ketone to give (XIII)(cf., for example, Tetrahedron Lett. 1978, 2111; Tetrahedron Lett. 1981,5251; Chem. Ber. 1960, 2294; J. Chem. Soc. Perkin Trans. 1, 1991, 1467;Tetrahedron Lett. 1992, 8091). The resulting unsaturated cyclic ketoneof the formula XIII can be reacted with a hydrazine in a manner knownper se (cf., for example, A. R. Katritzky et al. ComprehensiveHeterocyclic Chemistry, Vol. 2, 6 (1984), Pergamon Press; J.Heterocyclic Chem. 1969, 533; J. Heterocyclic Chem. 1968, 853), wherethe resulting pyrazoline can be modified further by customary processes.

It is furthermore possible to react the unsaturated cyclic ketone of theformula XIII with hydroxylamine or equivalents thereof (Z. Chem. 1980,20, 19). This gives the corresponding isoxazoline derivatives, which canbe modified further by customary processes.

Furthermore, it is possible to convert aldehydes of the formula XIV,which can be prepared in a manner known per se, analogously to processesknown from the literature by reaction with a hydrazine or hydroxylamine(or equivalents of these) into the corresponding hydrazones or oximes(cf., for example, Synth. Commun. 1990, 20, 1373; J. Org. Chem. 1980,45, 3756). These in turn can be converted in a manner known per se intothe corresponding 1,3-dipoles, which then react in a [3+2]-cycloadditionto give the compounds VIc (cf., for example, Synth. Commun. 1990, 20,1373; EP-A 386 892; J. Org. Chem. 1980, 45, 3756; Tetrahedron Lett.1981, 22, 1333.)

The resulting pyrazoles or pyrazolines and isoxazoles or isoxazolinescan be modified further by customary processes.

It is also possible to react the cyclic ketone of the formula XI with adithiol or a “mixed alcohol” analogously to processes known from theliterature (cf., for example, T. W. Greene et al., Protective Groups inOrganic Synthesis, John Wiley & Sons, 133–140), and to subject itsubsequently to a rearrangement in the presence of bromine or a suitableLewis acid, such as, for example, tellurium tetrachloride (cf.Tetrahedron 1991, 47, 4187; Synthesis 1991, 223; J. Chem. Soc. Chem.Commun. 1985, 1645).

The resulting heterocycles can, if desired, be modified further byprocesses known per se.

The abovementioned substituents R^(3a) are hydrogen, C₁–C₆-alkyl,C₁–C₆-haloalkyl, hydroxyl, C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;furthermore, the abovementioned radicals R^(3b) are hydrogen,C₁–C₆-alkyl or C₁–C₆-haloalkyl.

The tricyclic benzoic esters of the formula VIc or the tricyclic benzoicacids of the formula VIb can be obtained by reacting a tricyclic benzenederivative of the formula IX with a C₁–C₆-alcohol or water in thepresence of carbon monoxide, a catalyst and a base. In general, theconditions mentioned under process F apply.

L⁴ is a leaving group, such as halogen, for example chlorine, bromine oriodine, or sulfate, such as mesylate or triflate; preference is given tobromine or triflate.

Furthermore, the tricyclic benzoic acids of the formula VIb can beobtained by converting a tricyclic benzene derivative of the formula IXwhere L⁴ is halogen, such as chlorine or bromine, in particular bromine,by reaction with, for example, n-butyllithium or magnesium into themetalated derivative, followed by quenching with carbon dioxide (cf.,for example, J. Org. Chem. 1990, 55, 773; Angew. Chem. Int. Ed. 1969, 8,68).

It is also possible to obtain the tricyclic benzoic acids VIb byhydrolyzing the corresponding nitriles, analogously to processes knownfrom the literature. The nitriles for their part can be obtained byhalogen/nitrile exchange or by Sandmeyer reaction from the correspondinganilines XV.

The compounds of the formula IX,

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;    -   Y together with the two carbons to which it is attached forms a        saturated, partially saturated or unsaturated 5- or 6-membered        heterocycle which contains one to three identical or different        heteroatoms selected from the following group: oxygen, sulfur or        nitrogen;    -   R¹,R²,R⁶,R⁷ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;    -   R³ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy or        C₁–C₆-haloalkoxy;    -   R⁴ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,        C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,        C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,        C₁–C₆-haloalkylsulfonyl, aminosulfonyl,        N-(C₁–C₆-alkyl)aminosulfonyl, N,N-di(C₁–C₆-alkyl)aminosulfonyl,        N-(C₁–C₆-alkylsulfonyl)amino, N-(C₁–C₆-haloalkylsulfonyl)amino,        N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino or        N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino;    -   R⁵ is hydrogen, C₁–C₆-alkyl or halogen;    -   R⁸ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkylcarbonyl, formyl, C₁–C₆-alkoxycarbonyl,        C₁–C₆-haloalkoxycarbonyl, C₁–C₆-alkylsulfonyl or        C₁–C₆-haloalkylsulfonyl;    -   l is 0, 1 or 2;    -   L⁴ is halogen, C₁–C₆-alkylsulfonyloxy,        C₁–C₆-haloalkylsulfonyloxy or phenylsulfonyloxy, where the        phenyl ring of the lastmentioned radical may be unsubstituted or        partially or fully halogenated and/or may carry one to three of        the following radicals: nitro, cyano, C₁–C₆-alkyl,        C₁–C₆-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy;        are novel.

Preference is given to compounds of the formula IX where L⁴ is halogen,in particular bromine.

The particularly preferred embodiments of the compounds of the formulaIX with respect to the variables X, Y, R¹ to R⁵ and l correspond tothose of the tricyclic benzoylpyrazole derivatives of the formula I.

Particular preference is given to the compounds of the formula IX where

-   -   Y together with the two carbons to which it is attached forms        the following heterocycles:

Here, extraordinary preference is given to the compounds IX where

-   -   R⁴ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy, C₁–C₆-alkylthio or C₁–C₆-alkylsulfonyl; in        particular C₁–C₆-alkylsulfonyl.

The compounds of the formula IX can be obtained in different ways, thefused system, for example, can be constructed analogously to theprocesses described for the compounds of the formula VIc.

However, it is also possible to construct the fused system from asuitable parent compound (analogously to the processes described forcompounds of the formula VIc) and to introduce L⁴=halogen subsequentlyby customary halogenating reactions.

The anilines of the formula XV and the nitrites of the formula XVI

where:

-   -   X is oxygen, sulfur, S═O, S(═O)₂, CR⁶R⁷, NR⁸ or a bond;    -   Y together with the two carbons to which it is attached forms a        saturated, partially saturated or unsaturated 5- or 6-membered        heterocycle which contains one to three identical or different        heteroatoms selected from the following group:    -    oxygen, sulfur or nitrogen;    -   R¹,R²,R⁶,R⁷ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy or C₁–C₆-haloalkoxy;    -   R³ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy or        C₁–C₆-haloalkoxy;    -   R⁴ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,        C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,        C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,        C₁–C₆-haloalkylsulfonyl, aminosulfonyl,        N-(C₁–C₆-alkyl)aminosulfonyl, N,N-di(C₁–C₆-alkyl)aminosulfonyl,        N-(C₁–C₆-alkylsulfonyl)amino, N-(C₁–C₆-haloalkylsulfonyl)amino,        N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino or        N-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino;    -   R⁵ is hydrogen, C₁–C₆-alkyl or halogen;    -   R⁸ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkylcarbonyl, formyl, C₁–C₆-alkoxycarbonyl,        C₁–C₆-haloalkoxycarbonyl, C₁–C₆-alkylsulfonyl or        C₁–C₆-haloalkylsulfonyl;    -   l is 0, 1 or 2;        are also novel.

The particularly preferred embodiments of the compounds of the formulaeXV and XVI with respect to the variables X, Y, R¹ to R⁵ and l correspondto those of the tricyclic benzoylpyrazole derivatives of the formula I.

Particular preference is given to the compounds of the formula XV or XVIwhere

-   -   Y together with the two carbons to which it is attached forms        the following heterocycles:

Here, extraordinary preference is given to the compounds XV or XVI where

-   -   R⁴ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,        C₁–C₆-alkoxy, C₁–C₆-alkylthio or C₁–C₆-alkylsulfonyl; in        particular C₁–C₆-alkylsulfonyl.

The compounds of the formula XV can be obtained in different ways; forexample, the fused system can be constructed analogously to theprocesses described for the compounds of the formula VIc.

However, it is also possible to construct the fused system from asuitable parent compound (analogously to the processes described for thecompounds of the formula VIc) and to introduce a nitro groupsubsequently by nitration para to R⁴, analogously to processes knownfrom the literature, and to convert this group in a manner known per seby reduction into the amino group.

If appropriate, it may be advantageous in the synthesis variantsdescribed above to introduce protective groups for certainfunctionalities if the functionalities are not compatible with thereaction conditions required.

The selection of the protective groups depends both on the reactionconditions and on the structure of the molecule. The protective groups,their introduction and their removal are generally known from theliterature (cf., for example, T. W. Greene et al., “Protective Groups inOrganic Synthesis”, 2^(nd) edition, Wiley, New York, 1991), and they canbe employed analogously to processes known from the literature.

Furthermore, it may be necessary to carry out a combination of thesynthesis variants described above.

It is also possible to introduce further substituents or to modify thesubstituents present by electrophilic, nucleophilic, free-radical ororganometallic reactions and by oxidation or reduction reactions.

PREPARATION EXAMPLES 1.(5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methyl-sulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone(compound 2.2) 2-Allyl-6-chlorobenzaldehyde

Under an atmosphere of protective gas, a solution of 10.89 g (0.107 mol)of trimethylethylenediamine in 50 ml of anhydrous tetrahydrofuran wascooled to −10° C. and admixed dropwise with 66.6 ml of a 1.6 molarsolution of n-butyllithium in hexane (0.107 mol). After 10 minutes, 15 g(0.107 mol) of 6-chlorobenzaldehyde in 70 ml of tetrahydrofuran wereadded dropwise, and the mixture was admixed with a further 0.214 mol ofn-butyllithium in hexane (146.8 ml) and stirred at 0° C. for 2.5 hours.The mixture was cooled to −200° C., 12.42 g (0.139 mol) of copper(I)cyanide were added, the mixture was stirred at −10° C. for 30 minutes,and 28.42 g of allyl bromide in 100 ml of tetrahydrofuran were thenadded dropwise. The mixture was stirred at 0° C. for another 2.5 hours,and 230 ml of saturated ammonium chloride solution were then addeddropwise. The resulting solid was separated off and the aqueous phasewas extracted with diethyl ether. The combined organic phases were thenwashed with saturated ammonium chloride solution and dried, and thesolvent was removed under reduced pressure. This gave 17.0 g of2-allyl-6-chlorobenzaldehyde (89%) in the form of a dark oil.

¹H NMR (CDCl₃, δ in ppm): 3.73 (d, 2H); 5.05 (dd, 2H); 5.96 (m, 1H);7.05–7.48 (m, 3H); 10.58 (s, 1H).

2-Allyl-6-chlorobenzaldehyde oxime

5.58 g of sodium bicarbonate were added to a solution of 4.62 g ofhydroxylamine hydrochloride in 50 ml of water, and the mixture wascooled to 0° C. A solution of 9.7 g (44.32 mmol) of2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was then addeddropwise, and the mixture was stirred at room temperature overnight. Themethanol was subsequently removed under reduced pressure and the residuewas stirred into 300 ml of water. The aqueous phase was extracted withdiethyl ether and the combined organic phases were washed with saturatedammonium chloride solution and dried, and the solvent was removed. Thisgave 8.7 g (quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in theform of a viscous oil.

¹H NMR (CDCl₃, δ in ppm): 3.58 (d, 2H); 5.02 (2d, 2H); 5.95 (m, 1H);7.08–7.36 (m, 3H); 8.49 (s, 1H).

8-Chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazole

At room temperature, 37.0 ml of a sodium hypochlorite solution (12.5% ofactive chlorine) were added dropwise to a solution of 8.4 g (42.9 mmol)of 2-allyl-6-chlorobenzaldehyde oxime in 100 ml of methylene chloride,and a spatula tip of sodium acetate was added. The mixture was stirredat room temperature for 2 hours, the organic phase was separated off,the aqueous phase was extracted with methylene chloride and the combinedorganic phases were washed with saturated ammonium chloride solution.The organic phase was dried and the solvent was removed. This gave 7.0 g(94%) of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in the form ofa viscous oil.

¹H NMR (CDCl₃, δ in ppm): 2.81 (dd, 1H); 3.24 (dd, 1H); 3.78–4.03 (s,2H); 4.78 (t, 1H); 7.23–7.41 (m, 3H).

8-Methylthio-3a,4-dihydro-3H-indeno[1,2c]isoxazole

At room temperature, 3.6 g (52.0 mmol) of sodium thiomethoxide wereadded to a solution of 5.0 g (25.8 mmol) of8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in 60 ml ofN-methylpyrrolidone, and the mixture was stirred overnight. The mixturewas subsequently stirred into 800 ml of water, the aqueous phase wasextracted with diethyl ether, the combined organic phases were washedwith saturated ammonium chloride solution and dried, and the solvent wasremoved. This gave 4.6 g (87%) of8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole in the form of adark brown solid.

¹H NMR (CDCl₃, δ in ppm): 2.54 (s, 3H); 2.78 (dd, 1H); 3.21 (dd, 1H);3.72–3.93 (s, 2H); 4.64 (t, 1H); 7.09–7.38 (m, 3H).

5-Bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole

120 ml of sulfuric acid (98 percent strength) were cooled to 0° C., and11.2 g (54.8 mmol) of8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole were added a littleat a time. 9.2 g (57.5 mmol) of bromine were then added dropwise, andstirring was continued at 0° C. for another 2 hours. The resultingsolution was poured into 2 l of a mixture of water and ice, this mixturewas stirred for 1.5 hours and the precipitated solid was filtered offwith suction and then washed and dried. This gave 11.4 g (73%) of5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole of a brownsolid having a m.p. of 127–135° C.

¹H NMR (CDCl₃, δ in ppm): 2.53 (s, 3H); 2.71 (dd, 1H); 3.24 (dd, 1H);3.81–4.02 (s, 2H); 4.71 (t, 1H); 7.01 (d, 1H); 7.47 (d, 1H).

5-Bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole

A solution of 11.2 g (39.4 mmol) of5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole and 1.55 gof sodium tungstate in 250 ml of toluene and 50 ml of glacial aceticacid was heated to 70° C. and mixed dropwise with 10.73 g (39 percentstrength, 86.8 mmol) of hydrogen peroxide. Stirring was continued at 70°C. for another 3 hours, and a solid precipitated out. The mixture wasallowed to cool to room temperature and stirred into 1 l of water, andthe white solid was filtered off with suction. The organic phase of thefiltrate was separated off and the aqueous phase was extracted withethyl acetate. The combined organic phases were washed with water anddried, and the solvent was removed. This gave a viscous brown oil whichwas stirred with hexane/ethyl acetate (4:1). The resulting precipitatewas filtered off with suction and combined with the solid obtainedabove. This gave 7.3 g (59%) of5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole.

¹H-NMR (d⁶-DMSO, δ in ppm): 2.93 (dd, 1H); 3.23 (dd, 1H); 3.41 (s, 3H);3.94 (dd, 1H); 4.16 (m, 1H); 4.81 (t, 1H); 7.82 (d, 1H); 8.03 (d, 1H).

(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone(compound 2.1)

0.62 g (6.33 mmol) of 5-hydroxy-1-methylpyrazole, 1.75 g (12.66 mmol) ofdry potassium carbonate, 1.28 g (12.67 mmol) of triethylamine and 0.22 g(0.30 mmol) of bis-(triphenylphosphane)palladium dichloride were addedto a suspension of 2.0 g (6.33 mmol) of5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole in 100ml of dioxane. In a miniautoclave, a carbon monoxide pressure of 20 barwas applied, the mixture was stirred for 5 minutes and the autoclave wasvented. This procedure was repeated 3 times. The autoclave wassubsequently heated to 1300° C., a carbon monoxide pressure of 20 barwas applied once more and the mixture was stirred for 24 hours. Aftercooling and venting, the solvent was removed, and the residue was takenup in water, adjusted to pH 11 and washed with methylene chloride. Themixture was subsequently acidified to pH 4 using 10 percent strengthhydrochloric acid and extracted with methylene chloride. The combinedorganic phases were washed with saturated ammonium chloride solution anddried, and the solvent was removed. This gave 0.58 g (25%) of(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazole)-methanonein the form of a dark oil.

¹H NMR (CDCl₃, δ in ppm): 3.03 (dd, 1H); 3.42 (s, 3H); 3.40 (m, 1H);3.51 (s, 3H); 4.05 (m, 2H); 4.85 (t, 1H); 7.57 (s, 1H); 7.92 (d, 1H);8.22 (d, 1H).

(5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methyl-sulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone(compound 2.2)

Under an atmosphere of protective gas, 0.18 g of triethylamine and 0.26g (1.82 mmol) of benzoyl chloride in 10 ml of tetrahydrofuran were addedat 0° C. to a suspension of 0.55 g (1.52 mmol) of(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazol-5-yl)methanonein 10 ml of tetrahydrofuran. The mixture was stirred overnight at roomtemperature, the solvent was removed, the residue was taken up in ethylacetate, washed with water and dried, and the solvent was removed. Thecrude product was purified by silica gel chromatography (mobile phase:ethyl acetate: hexane=1:1). This gave 0.22 g (31%) of(5-phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanonein the form of a yellow solid having a m.p. of 86–93° C.

¹H NMR (CDCl₃, δ in ppm): 3.22 (s, 3H); 3.34 (m, 2H); 3.81 (s, 3H); 3.98(m, 2H); 4.81 (t, 1H); 7.20–8.21 (m, 8H).

2. 4-(2-Methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)carbonyl-5-hydroxy-1-methyl-1H-pyrazole (compound 3.1) Methyl2-chlorosulfonyl-4-chlorobenzoate

At from 0 to 5° C., a solution of 60.9 g (0.88 mol) of sodium nitrite in100 ml of water was added dropwise to a solution of 139 g (0.75 mol) ofmethyl 2-amino-4-chlorobenzoate in 400 ml of concentrated hydrochloricacid and the mixture was stirred at 0° C. for another hour.

In a second apparatus, 3 g of copper(II) chloride, 3 g ofbenzyltriethylammonium chloride, 10 ml of water and 400 ml of1,2-dichloroethane were combined and 64 g (1 mol) of sulfur dioxide wereintroduced.

The diazonium salt described above was subsequently added at from 10 to150° C., and the mixture was slowly heated to 50° C. A further 54 g(0.84 mol) of sulfur dioxide were then introduced, and stirring wascontinued at 500° C. for another 30 minutes. After cooling, 7.4 g (0.1mol) of chlorine gas were then introduced at room temperature, stirringwas continued for 15 minutes and the phases which had formed were thenseparated. The organic phase was dried and the solvent was removed. Thisgave 207 g of methyl 2-chlorosulfonyl-4-chlorobenzoate.

¹H NMR (CDCl₃, δ in ppm): 4.00 (s, 3H); 7.75 (m, 2H); 8.18 (m, 1H)

Methyl 2-mercapto-4-chlorobenzoate

Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder were addeda little at a time to a suspension of 205 g (0.75 mol) of methyl2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated hydrochloricacid and 375 g of ice. The mixture was stirred for another 3 hours andslowly heated to 70° C. After 2 hours at this temperature, the mixturewas cooled. The reaction mixture was allowed to stand at roomtemperature for 12 hours and then extracted with ethyl acetate, thecombined organic phases were dried and the solvent was removed. Thisgave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.

¹H NMR (CDCl₃, δ in ppm): 3.95 (s, 3H); 4.88 (s, 1H); 7.10 (m, 1H); 7.30(m, 1H); 7.96 (d, 1H).

Methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate

179.5 g (1.3 mol) of potassium carbonate and, a little at a time, 94.5 g(0.62 mol) of 3-bromopropionic acid were added to a solution of 125.4 g(0.62 mol) of methyl 2-mercapto-4-chlorobenzoate in 1.5 l of acetone,and the reaction mixture was stirred at room temperature for 12 hours.The solvent was distilled off, the residue was taken up in water and themixture was extracted with diethyl ether. The aqueous phase was thenmade acidic using concentrated hydrochloric acid, and the resultingprecipitate was filtered off with suction and dried. This gave 150 g(88%) of methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate.

M.p.: 133 to 1360° C.

Methyl 5-chloro-4-oxothiochromane-8-carboxylate

At 70° C., 50 g (0.18 mol) of methyl2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate were added to 500 gof polyphosphoric acid, and the mixture was stirred for a further 30minutes. The reaction mixture was then stirred into water and theresulting precipitate was filtered off with suction and dried. This gave41.1 g (88%) of methyl 5-chloro-4-oxothiochromane-8-carboxylate.

¹H NMR (CDCl₃, δ in ppm): 3.08 (m, 4H); 3.96 (s, 3H); 7.14 (d, 1H); 7.95(d, 1H).

Methyl5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate

30 g (0.078 mol) of methyl 5-chloro-4-oxothiochromane-8-carboxylate in300 ml of N,N-dimethylformamide dimethyl acetal were refluxed for 6hours. Volatile components were then distilled off, the residue wastaken up in methylene chloride and the organic phase was washed withwater. Drying and removal of the solvent gave 35.3 g (97%) of methyl5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate.

¹H NMR (CDCl₃, δ in ppm): 3.18 (s, 6H); 3.80 (s, 2H); 3.95 (s, 3H); 7.24(d, 1H); 7.64 (s, 1H); 7.82 (d, 1H).

2-Methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole

1.3 g (29.2 mmol) of methylhydrazine were added dropwise to a solutionof 7.0 g (22.5 mmol) of methyl5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylatein 700 ml of ethanol, and the mixture was refluxed for 2 hours. Thesolvent was removed and the residue was chromatographed over silica gelusing ethyl acetate/cyclohexane (2:3) as mobile phase. This gave 4.0 g(60%) of2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole.

¹H NMR (CDCl₃, δ in ppm): 3.76 (s, 2H); 3.95 (s, 3H); 4.00 (s, 3H); 7.24(s, 1H); 7.36 (d, 1H); 7.70 (d, 1H).

2-Methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole

4.0 g (13.6 mmol) of2-methyl-6-methoxycarbonyl-9-chloro-[l]-thiochromano[4,3-c]pyrazole in100 ml of methanol/water (1:1) were refluxed with 0.8 g (20 mmol) ofsodium hydroxide for 1 hour. The organic solvent was removed underreduced pressure and the residue was extracted with ethyl acetate. Theaqueous phase was acidified using concentrated hydrochloric acid and theresulting precipitate was filtered off with suction and dried. This gave3.5 g (92%) of2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole

¹H NMR (CDCl₃, δ in ppm): 3.80 (s, 2H); 3.96 (s, 3H); 7.40 (d, 1H); 7.65(m, 2H).

4-(2-Methyl-9-chloro-[l]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydroxy-1-methyl-1H-pyrazole(compound 3.1)

A mixture of 0.60 g (2.1 mmol) of2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole and0.21 g (2.1 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml ofacetonitrile was stirred at room temperature overnight. The mixture wasadmixed with in each case 500 ml of ethyl acetate and 2% strength sodiumcarbonate solution, the resulting precipitate was filtered off, theorganic phase was dried and the solvent was removed. The residue wasthen refluxed with 0.59 g (4.3 mmol) of potassium carbonate in 5 ml of1,4-dioxane for 3 hours. After cooling, the mixture was extracted withdiethyl ether and the aqueous phase was acidified to pH 3. The resultingprecipitate was filtered off with suction and dried. This gave 0.14 g of4-(2-methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydroxy-1-methyl-1H-pyrazole.

M.p.: 168–1710° C.

3.(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone(compound 2.3) Methyl 2-hydroxy-3-formyl-4-methoxybenzoate

At from 0 to 5° C., a solution of 209.0 g (1.1 mol) of titaniumtetrachloride in 150 ml of methylene chloride was added dropwise to asolution of 50.1 g (0.275 mol) of methyl 2-hydroxy-4-methoxybenzoate and88 g (0.725 mol) of dichloromethoxymethane in 400 ml of methylenechloride, and the mixture was stirred at room temperature overnight. Themixture was then stirred into ice-water and extracted with methylenechloride. The combined organic phases were washed with sodiumbicarbonate solution, water and sodium chloride solution and dried, andthe solvent was then removed. Silica gel chromatography usingcyclohexane/ethyl acetate=1:1 gave 24.5 g (42%) of methyl2-hydroxy-3-formyl-4-methoxybenzoate in the form of a colorless solid ofm.p.: 123–1240° C.

¹H NMR (CDCl₃, δ in ppm): 3.92 (s, 3H); 3.98 (s, 3H); 6.49 (d, 1H); 8.19(d, 1H); 10.39 (s, 1H).

Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

At room temperature, 23.2 g (0.192 mol) of allyl bromide were addeddropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500ml of dimethyl sulfoxide, and the mixture was stirred at roomtemperature for 4 hours. The mixture was subsequently stirred into 1.5 lof 3% strength aqueous hydrochloric acid and extracted with ethylacetate. The combined organic phases were washed with water and dried,and the solvent was removed. Silica gel chromatography usingcyclohexane/ethyl acetate=1:2 gave 7.7 g (36%) of methyl2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

¹H NMR (CDCl₃, δ in ppm): 3.86 (s, 3H); 3.93 (s, 3H); 4.58 (d, 2H); 5.32(d, 1H); 5.39 (d, 1H); 6.15 (m, 1H); 6.79 (d, 1H); 8.04 (d, 1H); 10.41(s, 1H).

6-Methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline

Step a)

At room temperature, 4.6 g (18.4 mmol) of methyl2-allyloxy-3-formyl-4-methoxybenzoate in 70 ml of methanol were addeddropwise to a solution of 2.25 g (32.3 mmol) of hydroxylammoniumchloride and 2.7 g of pyridine in 70 ml of water. The mixture wasstirred at room temperature overnight, 150 ml of water were added, themixture was extracted with methylene chloride, the combined organicphases were washed with 3% strength aqueous hydrochloric acid and dried,and the solvent was removed. The resulting oxime has a melting point of126–1290° C.

Step b)

This oxime was reacted further without any further purification bydissolving it in 40 ml of methylene chloride, followed by dropwiseaddition of 15.0 ml (25.0 mmol) of sodium hypochlorite solution (12.5%of active chlorine). A spatula tip of sodium acetate was added and themixture was stirred at room temperature for 12 hours. The organic phasewas separated off, the aqueous phase was extracted with methylenechloride, the combined organic phases were washed with water and dried,and the solvent was removed. Silica gel chromatography usingcyclohexane/ethyl acetate=1:1 gave 2.2 g (49%) of6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazolinein the form of a colorless solid of m.p: 199–203° C.

¹H NMR (CDCl₃, δ in ppm): 3.84 (s, 3H); 3.98 (s, 3H); 3.8–4.0 (m, 2H);4.16 (dt, 1H); 4.63 (t, 1H); 4.84 (dd, 1H); 6.61 (d, 1H); 7.93 (d, 1H).

6-Methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline

At room temperature, a solution of 0.8 g (20.0 mmol) of sodium hydroxidein 7 ml of water was added dropwise to a solution of 2.1 g (8.0 mmol) of6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolinein 40 ml of methanol, and the mixture was refluxed for 6 hours. Aftercooling, the solvent was removed and the residue was taken up in about50 ml of water and washed with methylene chloride. The aqueous phase wassubsequently acidified using 10% strength hydrochloric acid (pH=1–2),and the precipitate was filtered off with suction, washed with water anddried at 600° C. This gave 1.7 g (86%) of6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazolinein the form of colorless crystals.

¹H NMR (CDCl₃, δ in ppm): 3.73 (dd, 1H); 3.89 (s, 3H); 3.84–3.95 (m,1H); 4.11 (dd, 1H); 4.54 (dd, 1H); 4.79 (dd, 1H); 6.61 (d, 1H); 7.81 (d,1H).

(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone(compound 2.3)

Step a)

At room temperature, 0.26 g (2.2 mmol) of thionyl chloride and a drop ofdimethylformamide were added to a solution of 0.50 g (2.0 mmol) of6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[(4,3-c)]isoxazolinein 30 ml of carbon tetrachloride, and the mixture was stirred at 40–50°C. for 3 hours. The solvent was subsequently removed under reducedpressure. This gave, in quantitative yield,6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c] isoxazoline(0.54 g) as a brownish oil.

Step b)

0.54 g (2 mmol) of6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline wasdissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to asolution of 0.2 g (2.0 mmol) of 1-methyl-5-hydroxypyrazole and 0.6 g(6.0 mmol) of triethylamine in 20 ml of acetonitrile. The mixture wasstirred at room temperature overnight, the solvent was removed, and theresidue was taken up in methylene chloride and washed with water. Thesolution was dried and the solvent was distilled off. The residue wasdissolved in 30 ml of dioxane and admixed with 0.42 g (3.0 mmol) ofpotassium carbonate, and the mixture was refluxed for 7 hours. Aftercooling, the solvent was distilled off under reduced pressure, theresidue was taken up in water and the solution was adjusted to pH=1using 10% strength hydrochloric acid. The solution was extracted withmethylene chloride, the combined organic phases were dried and thesolvent was subsequently removed. This gave 0.45 g (68%) of(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanoneof m.p. 236–238° C.

¹H NMR (CDCl₃, δ in ppm): 3.66 (s, 3H); 3.84–4.2 (m, 2H); 4.02 (s, 3H);4.12 (dd, 1H); 4.63–4.77 (m, 2H); 6.68 (d, 1H); 7.24 (s, 1H); 7.61 (d,1H).

4.[5-Hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone(compound 2.4)

0.54 g (2 mmol) of6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline wasdissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to asolution of 0.28 g (2.0 mmol) of1-(1,1-dimethyleth-1-yl)-5-hydroxy-1H-pyrazole and 0.6 g (6.0 mmol) oftriethylamine in 20 ml of acetonitrile. The mixture was stirred at roomtemperature overnight, the solvent was removed, and the residue wastaken up in methylene chloride and washed with water. The solution wasdried, and the solvent was distilled off. The residue was dissolved in30 ml of dioxane and admixed with 0.42 g (3.0 mmol) of potassiumcarbonate, and the mixture was refluxed for 7 hours. After cooling, thesolvent was distilled off under reduced pressure, the residue was takenup in water and the solution was adjusted to pH=1 using 10% strengthhydrochloric acid. The solution was extracted with methylene chloride,the combined organic phases were dried, and the solvent was subsequentlyremoved. This gave 0.3 g (40%) of[5-hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanonehaving a melting point of 223° C.–2250° C.

¹H NMR (CDCl₃, δ in ppm): 1.64 (s, 9H); 3.8–4.2 (m, 6H); 4.6–4.8 (m,2H); 6.68 (d, 1H); 7.44 (s, 1H); 7.62 (d, 1H).

In addition to the compounds above, other tricyclic benzoylpyrazolederivatives of the formula I which were prepared or are preparable in asimilar manner are listed in Tables 2 to

TABLE 2

Ia where 1 = 0, R⁵ = H, Y together with the two carbons to which it isattached forms the following isoxazoline:

physical data (m.p.[° C.]; ¹H NMR No. X R⁴ R¹⁰ R¹¹ R¹² [ppm]) 2.1 BondSO₂CH₃ OH CH₃ H 3.03(dd, 1H); 3.42(s, 3H); 3.51(s, 3H); 4.05(m, 2H);4.85(t, 1H); 7.57(s, 1H); 7.92(d, 1H); 8.22(d, 1H) 2.2 Bond SO₂CH₃OCOC₆H₅ CH₃ H 3.22(s, 3H); 3.34(m, 2H); 3.81(s, 3H); 3.98(m, 2H);4.81(t, 1H); 7.20–8.21(m, 8H); 2.3 O OCH₃ OH CH₃ H 236–238 2.4 O OCH₃ OHC(CH₃)₃ H 223–225 2.5 O OCH₃ OCO(3- CH₃ H oil F—C₆H₄)

TABLE 3

Ia where R⁵ = H, Y together with the two carbons to which it is attachedforms the following methyl-substituted pyrazole:

No. X R⁴ R¹⁰ R¹¹ R¹² physical data (m.p.[° C.]) 3.1 S Cl OH CH₃ H168–171 3.2 S Cl OH CH₂CH₃ H 115 3.3 S SCH₃ OH CH₃ H 245 3.4 S SCH₃ OHCH₂CH₃ H 222

TABLE 4

Ia where R⁵ = H, Y together with the two carbons to which it is attachedforms the following methyl-substituted pyrimidine:

physical data No. X R⁴ R¹⁰ R¹¹ R¹² (m.p.[° C.]; ¹H NMR [ppm]) 4.1 S ClOH CH₃ H 180° C. 4.2 S Cl OH CH₂CH₃ H 112° C.

TABLE 5

physical data Nr. X R⁴ R¹⁰ R¹¹ R¹² (m.p.[° C.]; ¹H NMR [ppm]) 5.1 O SCH₃OH CH₃ H 201

The compounds of the formula I and their agriculturally useful salts aresuitable, both in the form of isomer mixtures and in the form of thepure isomers, as herbicides. The herbicidal compositions comprisingcompounds of the formula I control vegetation on non-crop areas veryefficiently, especially at high rates of application. They act againstbroad-leaved weeds and grass weeds in crops such as wheat, rice, maize,soya and cotton without causing any significant damage to the cropplants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds of theformula I, or herbicidal compositions comprising them, can additionallybe employed in a further number of crop plants for eliminatingundesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in cropswhich tolerate the action of herbicides owing to breeding, includinggenetic engineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be used for example in the form of ready-to-sprayaqueous solutions, powders, suspensions, also highly-concentratedaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusts, materials for broadcasting, or granules, bymeans of spraying, atomizing, dusting, spreading or watering. The useforms depend on the intended purpose; in any case, they should guaranteethe finest possible distribution of the active compounds according tothe invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I and auxiliaries which are customarily used for formulating cropprotection agents.

Suitable for use as inert auxiliaries are essentially the following:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal-tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes or their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thetricyclic benzoylpyrazole derivatives of the formula I, either as suchor dissolved in an oil or solvent, can be homogenized in water by meansof a wetting agent, tackifier, dispersant or emulsifier. Alternatively,it is possible to prepare concentrates comprising active compound,wetting agent, tackifier, dispersant or emulsifier and, if desired,solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, e.g. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfateand magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight, of at least one active compound. Theactive compounds are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

The following formulation examples illustrate the preparation of suchformulations:

-   I. 20 parts by weight of the compound No. 2.2 are dissolved in a    mixture composed of 80 parts by weight of alkylated benzene, 10    parts by weight of the adduct of from 8 to 10 mol of ethylene oxide    to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of    calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of    the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.    Pouring the solution into 100,000 parts by weight of water and    finely distributing it therein gives an aqueous dispersion which    comprises 0.02% by weight of the active compound.-   II. 20 parts by weight of the compound No. 3.1 are dissolved in a    mixture composed of 40 parts by weight of cyclohexanone, 30 parts by    weight of isobutanol, 20 parts by weight of the adduct of 7 mol of    ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of    the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.    Pouring the solution into 100,000 parts by weight of water and    finely distributing it therein gives an aqueous dispersion which    comprises 0.02% by weight of the active compound.-   III. 20 parts by weight of the compound No. 2.3 are dissolved in a    mixture composed of 25 parts by weight of cyclohexanone, 65 parts by    weight of a mineral oil fraction of boiling point 210 to 280° C. and    10 parts by weight of the adduct of 40 mol of ethylene oxide to 1    mol of castor oil. Pouring the solution into 100,000 parts by weight    of water and finely distributing it therein gives an aqueous    dispersion which comprises 0.02% by weight of the active compound.-   IV. 20 parts by weight of the compound No. 2.4 are mixed thoroughly    with 3 parts by weight of the sodium salt of    diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium    salt of a lignosulfonic acid from a sulfite waste liquor and 60    parts by weight of pulverulent silica gel, and the mixture is ground    in a hammer mill. Finely distributing the mixture in 20,000 parts by    weight of water gives a spray mixture which comprises 0.1% by weight    of the active compound.-   V. 3 parts by weight of the compound No. 2.3 are mixed with 97 parts    by weight of finely divided kaolin. This gives a dust which    comprises 3% by weight of the active compound.-   VI. 20 parts by weight of the compound No. 2.4 are mixed intimately    with 2 parts by weight of calcium salt of dodecylbenzenesulfonic    acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts    by weight of sodium salt of a phenol/urea/formaldehyde condensate    and 68 parts by weight of a paraffinic mineral oil. This gives a    stable oily dispersion.-   VII. 1 part by weight of the compound No. 2.2 is dissolved in a    mixture composed of 70 parts by weight of cyclohexanone, 20 parts by    weight of ethoxylated isooctylphenol and 10 parts by weight of    ethoxylated castor oil. This gives a stable emulsion concentrate.-   VIII. 1 part by weight of the compound No. 3.1 is dissolved in a    mixture composed of 80 parts by weight of cyclohexanone and 20 parts    by weight of Wettol® EM 31 (=nonionic emulsifier based on    ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can beapplied pre- or post-emergence. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that as far as possible they do notcome into contact with the leaves of the sensitive crop plants, whilethe active compounds reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The rates of application of the compound of the formula I are from 0.001to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.),depending on the control target, the season, the target plants and thegrowth stage.

To widen the spectrum of action and to achieve synergistic effects, thetricyclic benzylpyrazole derivatives of the formula I may be mixed witha large number of representatives of other herbicidal orgrowth-regulating active compound groups and applied concomitantly.Suitable components for mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, aryloxy-/heteroaryloxyalkanoic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-aroyl-1,3-cyclohexanediones, heteroaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinoline carboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formulaI, alone or in combination with other herbicides, in the form of amixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

Use Examples

The herbicidal activity of the tricyclic benzylpyrazole derivatives ofthe formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic pots containing loamy sand withapproximately 3.0% of humus as the substrate. The seeds of the testplants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this was adverselyaffected by the active compounds.

For post-emergence treatment, the test plants were first grown to aplant height of from 3 to 15 cm, depending on the plant habit, and onlythen treated with the active compounds which had been suspended oremulsified in water. For this purpose, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to the treatment. The application rate for the post-emergencetreatment was 0.5 or 0.25 kg of a.s./ha.

Depending on the species, the plants were kept at 10–25° C. or 20–35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least theabove-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse trials were of the following species:

Scientific Name Common Name Chenopodium album lambsquarters (goosefoot)Echinochloa crusgalli barnyardgrass Setaria viridis green foxtailSolanum nigrum black nightshade Veronica ssp. speadwell

At application rates of 0.5 or 0.25 kg/ha, the compound 2.2 shows verygood activity against the abovementioned undesired broad-leaved weedsand weed grasses when applied by the post-emergence method.

1. A tricyclic benzoylpyrazole compound of formula I

where: X is a bond; Y together with the two carbons to which it isattached forms a 1,2-isoxazole ring which is saturated, partiallysaturated or unsaturated; R¹, R², R⁶, R⁷ are hydrogen, C₁–C₆-alkyl,C₁–C₆-haloalkyl, C₁–C₆-alkoxy or C₁–C₆-haloalkoxy; R³ is halogen,C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy or C₁–C₆-haloalkoxy; R⁴ ishydrogen, nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio,C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,C₁–C₆-haloalkylsulfonyl, aminosulfonyl, N-(C₁–C₆-alkyl)aminosulfonyl,N,N-di(C₁–C₆-alkyl)aminosulfonyl, N-(C₁–C₆-alkylsulfonyl)amino,N-(C₁–C₆-haloalkylsulfonyl)amino,N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino orN-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino; R⁵ is hydrogen,C₁–C₆-alkyl or halogen; R⁸ is hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl,C₁–C₆-alkylcarbonyl, formyl, C₁–C₆-alkoxycarbonyl,C₁–C₆-haloalkoxycarbonyl, C₁–C₆-alkylsulfonyl orC₁–C₆-haloalkylsulfonyl; l is 0, 1 or 2; R⁹ is a radical IIa

 where R¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴, NR¹⁵R¹⁶or N-bonded heterocyclyl, where the heterocyclyl radical may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals:  nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl,C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹¹ is hydrogen, C₁–C₆-alkyl,C₁–C₆-haloalkyl, C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy orC₁–C₆-haloalkoxy; R¹² is hydrogen, halogen, C₁–C₆-alkyl,C₁–C₆-haloalkyl, hydroxyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy,C₁–C₆-alkylthio or C₁–C₆-haloalkylthio; R¹³ is C₁–C₆-alkyl,C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl,C₃–C₆-cycloalkyl, C₁–C₂₀-alkylcarbonyl, C₂–C₂₀-alkenylcarbonyl,C₂–C₆-alkynylcarbonyl, C₃–C₆-Cycloalkylcarbonyl, C₁–C₆-alkoxycarbonyl,C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl,C₁–C₆-alkylthiocarbonyl, C₁–C₆-alkylaminocarbonyl,C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl,N,N-di(C₁–C₆-alkyl)aminocarbonyl,N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,N-(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,N-(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,N-(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,di(C₁–C₆-alkyl)aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl,C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl orN,N-di(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, where the abovementionedalkyl, cycloalkyl and alkoxy radicals may be partially or fullyhalogenated and/or may carry one to three of the following groups: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di(C₁–C₄-alkyl)amino,C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,C₁–C₄-alkylaminocarbonyl, di(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl,C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;  is phenyl, heterocyclyl,phenyl-C₁–C₆-alkyl, heterocyclyl-C₁–C₆-alkyl,phenylcarbonyl-C₁–C₆-alkyl, heterocyclylcarbonyl-C₁–C₆-alkyl,phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl,phenyloxythiocarbonyl, heterocyclyloxycarbonyl,heterocyclyloxythiocarbonyl, phenylaminocarbonyl,N-(C₁–C₆-alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl,N-(C₁–C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,phenyl-C₂–C₆-alkenylcarbonyl or heterocyclyl-C₂–C₆-alkenylcarbonyl,where the phenyl and the heterocyclyl radical of the 18 lastmentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals:  nitro, cyano, C₁–C₄-alkyl,C₁–C₄-haloalkyl, C₁–C₄-alkoxy, C₁–C₄-haloalkoxy, heterocyclyl orN-bonded heterocyclyl, where the two lastmentioned substituents fortheir part may be partially or fully halogenated and/or may carry one tothree of the following radicals:  nitro, cyano, C₁–C₄-alkyl,C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁴ is C₁–C₆-alkyl,C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl,C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, di(C₁–C₆-alkyl)amino ordi(C₁–C₆-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl andalkoxy radicals may be partially or fully halogenated and/or may carryone to three of the following groups:  cyano, C₁–C₄-alkoxy,C₁–C₄-alkylthio, di(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl,C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,C₁–C₄-alkylaminocarbonyl, di(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl,C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;  is phenyl, heterocyclyl,phenyl-C₁–C₆-alkyl, heterocyclyl-C₁–C₆-alkyl, phenoxy, heterocyclyloxy,where the phenyl and the heterocyclyl radical of the lastmentionedsubstituents may be partially or fully halogenated and/or may carry oneto three of the following radicals:  nitro, cyano, C₁–C₄-alkyl,C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁵ is C₁–C₆-alkyl,C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl,C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy,di(C₁–C₆-alkyl)amino or C₁–C₆-alkylcarbonylamino, where theabovementioned alkyl, cycloalkyl and alkoxy radicals may be partially orfully halogenated and/or may carry one to three radicals of thefollowing group:  cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio,di(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,di(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,C₁–C₄-alkylaminocarbonyl, di(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl,C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;  is phenyl, heterocyclyl,phenyl-C₁–C₆-alkyl or heterocyclyl-C₁–C₆-alkyl, where the phenyl orheterocyclyl radical of the four lastmentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing radicals:  nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl,C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁶ is C₁–C₆-alkyl, C₃–C₆-alkenyl,C₃–C₆-alkynyl or C₁–C₆-alkylcarbonyl; or an agriculturally useful saltthereof.
 2. The tricyclic benzoylpyrazole compound of formula I definedin claim 1 where R¹, R² are hydrogen; R³ is C₁–C₆-alkyl; R⁴ is nitro,halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio orC₁–C₆-alkylsulfonyl; R⁵ is hydrogen; l is 0 or
 1. 3. The tricyclicbenzoylpyrazole compound of formula I defined in claim 1 where R¹⁰ ishydroxyl; R¹¹ is C₁–C₆-alkyl or C₃–C₆-cycloalkyl; R¹² is hydrogen orC₁–C₆-alkyl.
 4. A process for preparing the compound of formula I whereR¹⁰=halogen as claimed in claim 1, which comprises reacting a tricyclicbenzoylpyrazole compound of formula Iα (=I where R¹⁰=hydroxyl),

where the variables R¹ to R³, R¹¹ and R¹², X, Y and l are as defined inclaim 1, with a halogenating agent.
 5. A process for preparing thecompound of formula I where R¹⁰=OR¹³ as claimed in claim 1, whichcomprises reacting a tricyclic benzoylpyrazole compound of formula Iα(=I where R¹⁰=hydroxyl),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined inclaim 1, with a compound of formula IIIL¹—R¹³  III where the variable R¹³ is as defined in claim 1 and L¹ is anucleophilically replaceable leaving group.
 6. A process for preparingthe compound of formula I where R¹⁰=OR¹³, SR¹³, NR¹⁵R¹⁶ or N-bondedheterocyclyl as claimed in claim 1, which comprises reacting a compoundof formula Iβ (≡I where R¹⁰=halogen),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined inclaim 1, with a compound of formula IVα, IVβ, IVγ or IVδ HOR¹³ HSR¹³NHR¹⁵R¹⁶ H(N-bonded heterocyclyl) IVα IVβ IVγ IVδ

where the variables R¹³ to R¹⁶ are as defined in claim 1, optionally inthe presence of a base.
 7. A process for preparing the compound offormula I where R¹⁰=SO₂R¹⁴ as claimed in claim 1, which comprisesreacting a compound of formula Iγ (≡I where R¹⁰=SR¹⁴),

where the variables R¹ to R⁵, R¹¹ and R¹², X, Y and l are as defined inclaim 1, with an oxidizing agent.
 8. A process for preparing thecompound of formula I as claimed in claim 1, which comprises reacting ametalated pyrazole compound of formula V where M is a metal and R¹⁰ toR¹² are as defined in claim 1, except for R¹⁰=hydroxyl and mercapto,with a tricyclic benzoic acid compound of formula VIα where R¹ to R⁵, X,Y and l are as defined in claim 1 and L² is a nucleophilicallyreplaceable leaving group


9. A process for preparing the compound of formula Iα (=I whereR¹⁰=hydroxyl) as claimed in claim 1, which comprises acylating apyrazole of formula VII in which the variables R¹¹ and R¹² are asdefined in claim 1

with an activated tricyclic benzoic acid of formula VIβ or with atricyclic benzoic acid of formula VIγ,

where the variables R¹ to R⁵, X, Y and l are as defined in claim 1 andL³ is a nucleophilically replaceable leaving group, and rearranging theacylation product, optionally in the presence of a catalyst.
 10. Aprocess for preparing the compound of formula Iα (≡I where R¹⁰=hydroxyl)as claimed in claim 1, which comprises reacting a pyrazole of formulaVII in which the variables R¹¹ and R¹² are as defined in claim 1, or analkali metal salt thereof,

with a tricyclic benzene compound of formula IX where L⁴ is a leavinggroup and the variables X, Y, R¹ to R⁵ and l are as defined in claim 1

in the presence of carbon monoxide, a catalyst and a base.
 11. Acomposition, comprising a herbicidally effective amount of at least onecompound of formula I or an agriculturally useful salt thereof asclaimed in claim 1 and auxiliaries which are customary for formulatingcrop protection agents.
 12. A process for preparing the compositiondefined in claim 11, which comprises mixing a herbicidally effectiveamount of at least one compound of formula I or an agriculturally usefulsalt thereof and auxiliaries which are customary for formulating cropprotection agents.
 13. A method for controlling undesirable vegetation,which comprises allowing a herbicidally effective amount of at least onecompound of formula I or an agriculturally useful salt thereof asclaimed in claim 1 to act on plants, their habitat or on seed.
 14. Atricyclic benzoic acid compound of formula VI

in which the variables X, Y, R¹ to R³ and R⁵ and l are as defined inclaim 1 and R⁴ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio,C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,C₁–C₆-haloalkylsulfonyl, aminosulfonyl, N-(C₁–C₆-alkyl)aminosulfonyl,N,N-di(C₁–C₆-alkyl)aminosulfonyl, N-(C₁–C₆-alkylsulfonyl)amino,N-(C₁–C₆-haloalkylsulfonyl)amino,N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino orN-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino; R¹⁷ is hydroxyl or aradical which can be removed by hydrolysis.
 15. A tricyclic benzenecompound of formula IX

in which the variables X, Y, R¹ to R³ and R⁵ and l are as defined inclaim 1 and R⁴ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl,aminosulfonyl, N-(C₁–C₆-alkyl)aminosulfonyl,N,N-di(C₁–C₆-alkyl)aminosulfonyl, N-(C₁–C₆-alkylsulfonyl)amino,N-(C₁–C₆-haloalkylsulfonyl)amino,N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino orN-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino; R⁵ is hydrogen orC₁–C₆-alkyl; L⁴ is halogen, C₁–C₆-alkylsulfonyloxy,C₁–C₆-haloalkylsulfonyloxy or phenylsulfonyloxy, where the phenyl ringof the lastmentioned radical may be unsubstituted or partially or fullyhalogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy orC₁–C₄-haloalkoxy.
 16. An aniline compound of formula XV

in which the variables X, Y, R¹ to R³ and R⁵ and l are in each case asdefined in claim 1 and R⁴ is nitro, halogen, cyano, C₁–C₆-haloalkyl,C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio,C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,C₁–C₆-haloalkylsulfonyl, aminosulfonyl, N-(C₁–C₆-alkyl)aminosulfonyl,N,N-di(C₁–C₆-alkyl)aminosulfonyl, N-(C₁–C₆-alkylsulfonyl)amino,N-(C₁–C₆-haloalkylsulfonyl)amino,N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino orN-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino.
 17. A nitrile compoundof formula XVI

in which the variables X, Y, R¹ to R³ and l are in each case as definedin claim 1 and R⁴ is nitro, halogen, cyano, C₁–C₆-haloalkyl,C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,C₁–C₆-haloalkinylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl,aminosulfonyl, N-(C₁–C₆-alkyl)aminosulfonyl,N,N-di-(C₁–C₆-alkyl)aminosulfonyl, N-(C₁–C₆-alkylsulfonyl)amino,N-(C₁–C₆-haloalkylsulfonyl)amino,N-(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino orN-(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino; R⁵ is hydrogen orC₁–C₆-alkyl.
 18. The compound of formula I defined in claim 1, whereinR¹⁰ is hydroxyl, mercapto, halogen, OR¹³, SR¹³, SO₂R¹⁴ or NR¹⁵R¹⁶.